In [1]:

    

import multiprocessing
import bz2

import logging
import os
import sys
import re
import tarfile
import itertools

import nltk
from nltk.collocations import TrigramCollocationFinder
from nltk.metrics import BigramAssocMeasures, TrigramAssocMeasures

import gensim
from gensim.parsing.preprocessing import STOPWORDS
from gensim.utils import smart_open

import textblob

logging.basicConfig(format='%(levelname)s : %(message)s', level=logging.INFO)
logging.root.level = logging.INFO  # ipython sometimes messes up the logging setup; restore


    

In [2]:

    

gensim.utils.lemmatize("The quick brown fox jumps over the lazy dog!")


    

    
Out[2]:





['quick/JJ', 'brown/JJ', 'fox/NN', 'jump/NN', 'lazy/JJ', 'dog/NN']

In [3]:

    

def process_article((title, text)):
    """
    Parse a wikipedia article, returning its content as
    `(title, list of tokens)`, all utf8.
 
    """
    text = gensim.corpora.wikicorpus.filter_wiki(text) # remove markup, get plain text
    # tokenize plain text, throwing away sentence structure, short words etc
    tokens = gensim.utils.lemmatize(text, stopwords=STOPWORDS)
    #tokens = gensim.utils.simple_preprocess(text)
    return title.encode('utf8'), tokens

def convert_wikibooks(infile, processes=multiprocessing.cpu_count()):
    """
    Yield articles from a bz2 Wikibooks dump `infile` as (title, tokens) 2-tuples.
 
    Only articles of sufficient length are returned (short articles & redirects
    etc are ignored).
 
    Uses multiple processes to speed up the parsing in parallel.
 
    """
    texts = gensim.corpora.wikicorpus._extract_pages(bz2.BZ2File(infile)) # generator
    ignore_namespaces = 'Wikipedia Category File Portal Template MediaWiki User Help Book Draft'.split()
    # process the corpus in smaller chunks of docs, because multiprocessing.Pool
    # is dumb and would try to load the entire dump into RAM...
    for title, text, pageid in gensim.corpora.wikicorpus._extract_pages(smart_open(infile)):
        title, tokens = process_article((title, text))
        if len(tokens) < 50 or any(title.startswith(ns + ':') for ns in ignore_namespaces):
            continue  # ignore short articles and various meta-articles
        yield title.replace('\t', ' '), tokens, pageid


    

In [4]:

    

i = 0
for title, tokens, pageid in convert_wikibooks('data/enwikibooks-20150314-pages-articles.xml.bz2'):
    print "%s\n%s\n%s" % (title, ','.join(tokens), pageid)
    print
    i += 1
    if i > 10:
        break


    

    




Organic Chemistry/Cover
welcome/JJ,world/NN,foremost/RB,open/JJ,content/NN,organic/JJ,chemistry/NN,textbook/NN,web/NN,content/NN,image/NN,ethane/NN,png/NN,free/JJ,online/JJ,text/NN,intend/VB,complete/JJ,replacement/NN,printed/JJ,book/NN,study/NN,organic/JJ,chemistry/NN,organic/JJ,chemistry/NN,primarily/RB,devote/VB,unique/JJ,property/NN,carbon/NN,atom/NN,compound/NN,compound/NN,play/VB,critical/JJ,role/NN,biology/NN,ecology/NN,earth/NN,science/NN,geology/NN,physics/NN,industry/NN,medicine/NN,course/NN,chemistry/NN,glance/NN,new/JJ,material/NN,organic/JJ,chemistry/NN,bring/VB,table/NN,complicated/JJ,daunting/NN,concentration/NN,perseverance/NN,million/NN,student/NN,successfully/RB,pass/VB,course/NN,field/NN,chemistry/NN,base/VB,formula/NN,reaction/NN,molecule/NN,different/JJ,condition/NN,typical/JJ,general/NN,chemistry/NN,question/NN,ask/VB,student/NN,compute/VB,answer/NN,equation/NN,chapter/NN,memorize/VB,typical/JJ,organic/JJ,chemistry/NN,question/NN,line/NN,product/NN,form/VB,substance/NN,treat/VB,solution/NN,bombard/VB,light/NN,key/JJ,learn/VB,organic/JJ,chemistry/NN,understand/VB,cram/JJ,night/NN,test/NN,good/JJ,memorize/VB,mechanism/NN,michael/NN,addition/NN,superior/JJ,accomplishment/NN,ability/NN,explain/VB,reaction/NN,place/NN,thing/NN,easier/JJ,build/VB,body/NN,new/JJ,knowledge/NN,foundation/NN,solid/JJ,prior/NN,knowledge/NN,student/NN,serve/VB,knowledge/NN,bring/VB,subject/NN,subject/NN,general/JJ,chemistry/NN,concept/NN,particular/JJ,importance/NN,organic/JJ,chemist/NN,covalent/JJ,bond/VB,molecular/JJ,orbit/NN,theory/NN,vsepr/NN,modele/VB,understanding/JJ,acid/NN,base/NN,chemistry/NN,pka/NN,value/NN,trend/NN,periodic/JJ,table/NN,mean/VB,comprehensive/JJ,list/NN,knowledge/NN,gain/VB,order/NN,fully/RB,understand/VB,subject/NN,organic/JJ,chemistry/NN,idea/NN,thing/NN,need/VB,know/VB,succeed/VB,organic/JJ,chemistry/NN,test/NN,course/NN,organic/JJ,chemistry/NN,subject/NN,vary/VB,useful/JJ,close/JJ,daily/JJ,life/NN,try/VB,figure/VB,unknown/JJ,mystery/NN,daily/JJ,life/NN,factious/JJ,think/VB,habit/NN,generate/VB,superstition/NN,help/NN,chemistry/NN,help/VB,kind/NN,superstition/NN,try/VB,ultimate/JJ,truth/NN,convenience/NN,ancient/JJ,past/NN,struggle/VB,thing/NN,need/NN,context/NN,house/NN,food/NN,transportation/NN,burn/VB,question/NN,chemistry/NN,help/VB,daily/JJ,life/NN,answer/NN,question/NN,know/VB,subject/NN,thoroughly/RB,let/VB,start/VB
5

Organic Chemistry/Alkenes
alkene/NN,aliphatic/JJ,hydrocarbon/NN,contain/VB,carbon/NN,carbon/NN,double/JJ,bond/NN,general/JJ,formula/NN,cnh/NN,naming/NN,alkene/NN,alkene/NN,alkane/NN,ane/JJ,suffix/NN,change/VB,ene/VB,alkene/NN,contain/VB,double/JJ,bond/NN,double/JJ,bond/NN,terminal/JJ,double/JJ,bond/NN,end/NN,molecule/NN,necessary/JJ,place/VB,number/NN,butane/NN,ch/NN,ch/NN,ch/NN,ch/NN,butene/NN,ch/NN,chch/NN,ch/NN,double/JJ,bond/NN,terminal/JJ,carbon/NN,center/NN,chain/NN,carbon/NN,number/VB,way/NN,double/NN,bond/VB,carbon/NN,lowest/JJ,possible/JJ,number/NN,number/NN,precede/VB,ene/NN,suffix/NN,dash/NN,correct/JJ,pent/NN,ene/NN,ch/NN,ch/NN,chch/NN,ch/VB,incorrect/JJ,pent/NN,ene/NN,ch/NN,ch/NN,ch/NN,chch/VB,second/JJ,incorrect/JJ,flip/VB,formula/NN,horizontally/RB,result/NN,lower/JJ,number/NN,alkene/NN,double/JJ,bond/NN,alkene/NN,bond/NN,number/VB,molecule/NN,terminal/JJ,double/JJ,bond/NN,number/NN,lowest/JJ,highest/JJ,separated/JJ,comma/NN,iupac/JJ,numerical/JJ,prefix/NN,indicate/VB,number/NN,double/JJ,bond/NN,octa/JJ,diene/NN,ch/NN,ch/NN,chch/NN,chch/NN,ch/NN,ch/NN,deca/NN,diene/NN,ch/NN,chch/NN,ch/NN,ch/NN,chch/NN,ch/NN,ch/NN,ch/JJ,note/NN,number/VB,yield/NN,molecule/NN,double/JJ,bond/NN,separate/VB,single/JJ,bond/NN,double/JJ,bond/NN,condition/NN,conjugate/VB,represent/VB,enhanced/JJ,stability/NN,conformation/NN,energetically/RB,favore/VB,reactant/NN,situation/NN,combination/NN,ez/NN,notation/NN,earlier/RB,stereochemistry/NN,discuss/VB,ci/NN,tran/VB,notation/NN,ci/NN,mean/VB,tran/NN,mean/VB,opposite/JJ,alkene/NN,present/VB,unique/JJ,problem/NN,ci/NN,tran/VB,notation/NN,break/VB,thing/NN,mind/NN,alkene/NN,planar/JJ,rotation/NN,bond/NN,ll/VB,discuss/VB,later/RB,substituent/NN,double/JJ,bond/NN,stay/VB,cis/NN,ene/NN,tran/NN,ene/VB,example/NN,pretty/RB,straight/RB,forward/RB,left/NN,methyl/NN,group/NN,cis/JJ,ene/NN,right/NN,opposite/JJ,tran/NN,ene/RB,situation/NN,ci/NN,tran/VB,notation/NN,work/NN,fact/NN,correct/JJ,methylpent/NN,ene/NN,methylpent/NN,ene/NN,example/NN,use/VB,cis/NN,tran/NN,opposite/JJ,alkene/NN,differ/VB,substituent/NN,use/VB,ez/JJ,nomenclature/NN,come/VB,german/NN,word/NN,entgegen/NN,opposite/JJ,zusamman/NN,entgegen/NN,opposite/JJ,double/JJ,bond/NN,zusamman/NN,zame/VB,double/JJ,bond/NN,let/VB,begin/VB,methylpent/NN,ene/NN,begin/VB,divide/VB,alkene/NN,left/JJ,right/JJ,half/NN,assign/VB,substituent/NN,high/JJ,priority/NN,low/JJ,priority/NN,substituent/VB,priority/NN,base/VB,atomic/JJ,number/NN,substituent/NN,left/JJ,hydrogen/NN,lowest/JJ,priority/NN,atomic/JJ,number/NN,carbon/NN,higher/JJ,atomic/JJ,number/NN,right/JJ,carbon/NN,substituent/NN,bond/NN,carbon/NN,hydrogen/NN,high/JJ,priority/NN,low/JJ,priority/NN,high/JJ,priority/NN,zusamman/NN,mnemonic/JJ,think/NN,zame/VB,zide/RB,let/VB,look/VB,methylpent/NN,ene/NN,left/NN,substituent/NN,priority/NN,zusamman/NN,version/NN,substituent/NN,reverse/VB,right/JJ,high/JJ,priority/NN,substituent/NN,low/JJ,priority/NN,substituent/NN,high/JJ,low/JJ,priority/NN,opposite/JJ,left/JJ,right/RB,entgegen/NN,little/JJ,usually/RB,easier/JJ,alkene/NN,write/VB,little/JJ,practice/NN,ll/VB,easy/JJ,comparison/NN,ci/NN,tran/NN,ene/JJ,ene/JJ,image/NN,cis/NN,butene/NN,png/NN,image/NN,tran/NN,butene/NN,png/NN,cis/NN,ene/JJ,tran/NN,ene/JJ,certain/JJ,extent/NN,configuration/NN,regard/VB,cis/NN,isomer/NN,tran/NN,isomer/NN,correspondence/NN,exact/JJ,carbon/NN,atom/NN,identically/RB,substitute/VB,general/JJ,cis/NN,tran/NN,double/JJ,bond/VB,carbon/NN,atom/NN,hydrogen/NN,atom/NN,ch/NN,ch/NN,iupac/NN,gold/NN,book/NN,ci/NN,tran/VB,notation/NN,iupac/NN,gold/NN,book/NN,notation/NN,property/NN,alkene/NN,molecule/NN,carbon/NN,bond/VB,hydrogen/NN,contain/VB,sp/NN,hybridized/JJ,carbon/NN,atom/NN,carbon/NN,carbon/NN,double/JJ,bond/NN,carbon/NN,atom/NN,addition/NN,electron/NN,pair/NN,share/VB,sigma/NN,bond/NN,share/NN,pair/NN,electron/NN,pi/NN,bond/NN,general/JJ,formula/NN,aliphatic/JJ,alkene/NN,cnh/JJ,diastereomerism/VB,restricted/JJ,rotation/NN,characteristic/NN,pi/NN,bond/NN,alkene/NN,limited/JJ,rotation/NN,double/JJ,bond/NN,atom/NN,order/NN,alkene/JJ,structure/NN,rotate/VB,pi/NN,bond/NN,break/VB,require/VB,kcal/JJ,energy/NN,reason/NN,alkene/NN,different/JJ,chemical/NN,property/NN,base/VB,bond/NN,atom/NN,locate/VB,example/NN,ene/RB,exist/VB,diastereomer/NN,ene/JJ,ene/JJ,image/NN,cis/NN,butene/NN,png/NN,image/NN,tran/NN,butene/NN,png/NN,cis/NN,ene/JJ,tran/NN,ene/JJ,relative/JJ,stability/NN,observe/VB,reaction/NN,addition/NN,hydrogen/NN,butene/VB,butene/NN,butene/NN,product/NN,butane/NN,difference/NN,reaction/NN,reaction/NN,different/JJ,energy/NN,kcal/NN,mol/NN,butene/NN,kcal/NN,mol/NN,butene/NN,kcal/JJ,mol/NN,butene/NN,illustrate/VB,difference/NN,stability/NN,species/NN,butene/NN,isomer/NN,difference/NN,energy/NN,release/VB,reduce/VB,relative/JJ,stability/NN,alkene/NN,estimate/VB,base/VB,following/JJ,concept/NN,internal/JJ,double/JJ,bond/NN,terminal/JJ,carbon/NN,stable/JJ,terminal/NN,double/JJ,bond/NN,terminal/JJ,carbon/NN,internal/JJ,alkene/NN,stable/JJ,terminal/JJ,alkene/NN,connect/VB,carbon/NN,chain/NN,terminal/NN,alkene/NN,locate/VB,end/NN,chain/NN,double/JJ,bond/NN,connect/VB,carbon/NN,primary/JJ,primary/NN,carbon/NN,stable/NN,middle/NN,chain/NN,double/JJ,bond/NN,connect/VB,carbon/NN,secondary/JJ,stable/JJ,quaternary/JJ,general/JJ,bulkier/JJ,alkyl/JJ,group/NN,sp/NN,hybridized/JJ,carbon/NN,alkene/NN,stable/JJ,alkene/NN,tran/NN,double/JJ,bond/NN,stable/JJ,cis/JJ,double/JJ,bond/NN,reaction/NN,preparation/NN,method/NN,create/VB,alkene/NN,method/NN,wittig/NN,reaction/NN,ll/VB,briefly/NN,chapter/NN,instead/RB,cover/VB,later/RB,book/NN,know/VB,way/NN,create/VB,alkene/NN,haloalkanes/JJ,synthesis/NN,alkene/NN,halide/NN,convert/VB,alkene/NN,elimination/NN,element/NN,hydrogen/NN,halide/NN,involve/VB,removal/NN,halogen/NN,atom/NN,hydrogen/NN,atom/NN,carbon/NN,adjacent/JJ,bear/VB,halogen/NN,elimination/NN,mechanism/NN,ll/VB,discuss/VB,end/NN,chapter/NN,haloalkane/NN,hydrogen/NN,halide/NN,neighboring/JJ,carbon/NN,hydrogen/NN,halogen/NN,neighboring/JJ,carbon/NN,reaction/NN,place/NN,surprising/JJ,reagent/NN,require/VB,elimination/NN,molecule/NN,acid/NN,strong/JJ,base/NN,example/NN,alcholic/JJ,koh/NN,case/NN,reaction/NN,yield/NN,single/JJ,alkene/NN,case/NN,yield/VB,mixture/NN,butyl/NN,chloride/NN,example/NN,eliminate/VB,hydrogen/NN,yield/NN,butene/NN,sec/NN,butyl/NN,chloride/NN,hand/NN,eliminate/VB,hydrogen/NN,yield/NN,butene/NN,butene/NN,alkene/NN,form/VB,butene/NN,chief/JJ,product/NN,dehalogenation/NN,vicinal/JJ,synthesis/NN,alkene/NN,debromination/NN,vicinal/JJ,dihalide/NN,sodium/NN,iodide/NN,synthesis/NN,alkene/NN,debromination/NN,vicinal/JJ,dihalide/NN,zinc/NN,dehalogenation/NN,vicinal/JJ,halide/NN,neighboring/JJ,carbon/NN,think/VB,vicinity/NN,method/NN,synthesize/VB,alkene/NN,reaction/NN,place/NN,sodium/NN,iodide/NN,solution/NN,acetone/NN,perform/VB,zinc/NN,dust/NN,solution/NN,heated/JJ,ethanol/NN,acetic/JJ,acid/NN,reaction/NN,perform/VB,magnesium/NN,ether/NN,mechanism/NN,different/JJ,actually/RB,produce/VB,intermediate/JJ,grignard/NN,reagent/NN,react/VB,cause/VB,elimination/NN,result/VB,alkene/JJ,dehydration/NN,alcohol/NN,synthesis/NN,alkene/NN,dehydration/NN,alcohol/NN,alcohol/NN,convert/VB,alkene/NN,dehydration/NN,elimination/NN,molecule/NN,water/NN,dehydration/NN,require/VB,presence/NN,acid/NN,application/NN,heat/NN,generally/RB,carry/VB,way/NN,heat/VB,alcohol/NN,sulfuric/JJ,phosphoric/JJ,acid/NN,temperature/NN,high/JJ,pass/VB,alcohol/NN,vapor/NN,alumina/NN,al/NN,alumina/NN,serve/VB,lewis/JJ,acid/NN,ease/NN,dehydration/NN,alcohol/NN,isomeric/JJ,alkene/NN,form/VB,tendency/NN,isomer/NN,predominate/VB,sec/VB,butyl/JJ,alcohol/NN,yield/VB,butene/NN,butene/NN,actually/RB,yield/NN,exclusively/RB,isomer/NN,formation/NN,butene/NN,butyl/NN,alcohol/NN,illustrate/VB,characteristic/JJ,dehydration/NN,share/VB,double/JJ,bond/NN,form/VB,position/NN,remote/JJ,carbon/NN,originally/RB,hold/VB,group/NN,characteristic/JJ,account/VB,later/JJ,chiefly/RB,greater/JJ,certainty/NN,double/JJ,bond/NN,appear/VB,prefer/VB,dehydration/NN,method/NN,alkene/NN,reduction/NN,alkene/NN,reduction/NN,alkene/NN,double/JJ,bond/NN,stage/NN,triple/JJ,bond/NN,end/NN,chain/NN,yield/NN,cis/NN,alkene/NN,trans/NN,alkene/NN,isomer/NN,predominate/VB,depend/VB,choice/NN,reduce/VB,agent/NN,predominantly/RB,tran/VB,alkene/JJ,obtain/VB,reduction/NN,alkene/NN,sodium/NN,lithium/NN,liquid/JJ,ammonia/NN,entirely/RB,cis/JJ,alkene/NN,high/JJ,obtain/VB,hydrogenation/NN,alkene/NN,different/JJ,catalyst/NN,specially/RB,prepared/JJ,palladium/NN,lindlar/JJ,catalyst/NN,nickel/NN,boride/NN,catalyst/NN,reaction/NN,highly/RB,stereoselective/VB,cis/JJ,reduction/NN,alkyne/NN,attribute/VB,general/JJ,way/NN,attachment/NN,hydrogen/NN,alkyne/NN,sit/VB,catalyst/NN,surface/NN,presumably/RB,stereochemistry/NN,hold/VB,hydrogenation/NN,terminal/NN,alkene/NN,yield/VB,cis/NN,tran/VB,alkenes/JJ,wittig/NN,reaction/NN,synthesis/NN,alkene/NN,wittig/JJ,reaction/NN,markovnikov/NN,rule/NN,continue/VB,discuss/VB,reaction/NN,need/VB,detour/NN,discuss/VB,subject/NN,important/JJ,alkene/JJ,reaction/NN,markovnikov/VB,rule/NN,simple/JJ,rule/NN,state/VB,russian/JJ,vladmir/NN,markovnikov/NN,orientation/NN,addition/NN,hbr/NN,alkene/VB,rule/NN,state/NN,unsymmetrical/JJ,alkene/NN,react/VB,hydrogen/NN,halide/NN,alkyl/NN,halide/VB,hydrogen/NN,add/VB,carbon/NN,alkene/NN,greater/JJ,number/NN,hydrogen/NN,substituent/NN,halogen/NN,carbon/NN,alkene/NN,fewer/JJ,number/NN,hydrogen/NN,substituent/NN,rule/NN,compare/VB,phrase/NN,rich/JJ,richer/JJ,poor/JJ,poorer/NN,carbon/NN,hydrogen/NN,hydrogen/NN,hydrogen/NN,halogen/NN,mean/VB,nucleophile/NN,electophile/NN,nucleophile/JJ,pair/NN,bond/VB,position/NN,stable/JJ,carbocation/NN,partial/JJ,positive/JJ,charge/NN,case/NN,transition/NN,state/NN,example/NN,br/NN,attach/VB,middle/JJ,carbon/NN,terminal/JJ,carbon/NN,markovnikov/NN,rule/NN,markovnikov/JJ,product/NN,markovnikov/JJ,product/NN,product/NN,reaction/NN,follow/VB,markovnikov/VB,rule/NN,markovnikov/JJ,product/NN,markovnikov/NN,addition/NN,markovnikov/NN,addition/NN,addition/NN,reaction/NN,follow/VB,markovnikov/VB,rule/NN,produce/VB,markovnikov/JJ,product/NN,markovnikov/JJ,addition/NN,certain/JJ,reaction/NN,produce/VB,opposite/JJ,markovnikov/JJ,product/NN,yielding/NN,markovnikov/JJ,product/NN,hydrogen/NN,end/VB,substituted/JJ,carbon/NN,double/JJ,bond/NN,hydroboration/JJ,oxidation/NN,reaction/NN,ll/VB,discuss/VB,shortly/RB,example/NN,reaction/NN,conduct/VB,peroxide/NN,modernized/JJ,version/NN,markovnikov/NN,rule/NN,explain/VB,markovnikov/JJ,behavior/NN,original/JJ,markovnikov/NN,rule/NN,predict/VB,hydrogen/NN,electrophile/NN,add/VB,double/JJ,bond/NN,end/VB,carbon/NN,hydrogen/NN,generalize/VB,electrophile/VB,electrophile/NN,end/VB,carbon/NN,greatest/JJ,number/NN,hydrogen/NN,usually/RB,hydrogen/NN,play/VB,role/NN,electrophile/NN,hydrogen/NN,act/VB,nucleophile/NN,reaction/NN,following/JJ,expansion/NN,markovnikov/NN,rule/NN,alkene/NN,undergo/VB,electrophilic/JJ,addition/NN,electrophile/NN,add/VB,carbon/NN,greatest/JJ,number/NN,hydrogen/NN,substituent/VB,nucleophile/NN,add/VB,highly/RB,substituated/JJ,carbon/NN,simply/RB,species/NN,add/VB,add/VB,carbon/NN,greatest/JJ,number/NN,hydrogen/NN,fact/NN,reaction/NN,reliably/RB,produce/VB,markovnikov/JJ,product/NN,actually/RB,powerful/JJ,tool/NN,organic/JJ,chemistry/NN,example/NN,reaction/NN,discuss/VB,ll/VB,different/JJ,way/NN,create/VB,alcohol/NN,alkene/NN,oxymercuration/JJ,reduction/NN,hydroboration/JJ,oxidation/NN,oxymercuration/NN,produce/VB,markovnikov/JJ,product/NN,hydroboration/NN,produce/VB,markovnikov/JJ,product/NN,organic/JJ,chemist/NN,choice/NN,product/NN,stick/VB,single/JJ,product/NN,desire/VB,work/VB,markovnikov/JJ,rule/NN,work/NN,stability/NN,carbocation/NN,intermediate/NN,experiment/NN,tend/VB,reveal/VB,carbocation/NN,planar/JJ,molecule/NN,carbon/NN,substituent/NN,vacant/JJ,orbital/JJ,perpendicular/JJ,rd/NN,plane/NN,orbital/JJ,extend/VB,trisubstituent/NN,plane/NN,lead/VB,stabilize/VB,effect/NN,happen/VB,unfilled/JJ,antibonding/NN,vacant/JJ,orbital/JJ,filled/JJ,bond/NN,orbital/JJ,result/NN,filled/JJ,orbital/JJ,interact/VB,unfilled/JJ,orbital/JJ,stabilize/VB,molecule/NN,highly/RB,substitute/VB,molecule/NN,chance/NN,stable/JJ,molecule/NN,stabilize/VB,effect/NN,inductive/JJ,effect/NN,exception/NN,rule/NN,exception/NN,markovnikov/JJ,rule/NN,tremendous/JJ,importance/NN,organic/JJ,synthesis/NN,hbr/NN,hydrogen/NN,peroxide/NN,formation/NN,free/JJ,radical/NN,mechanism/NN,react/VB,alkyl/JJ,free/JJ,radical/JJ,form/NN,middle/JJ,atom/NN,stable/JJ,hydrogen/NN,attach/VB,note/VB,hydrogen/NN,addition/NN,second/JJ,step/NN,example/NN,addition/NN,reaction/NN,hydroboration/NN,hydroboration/NN,useful/JJ,reaction/NN,alkene/NN,end/NN,product/NN,intermediate/JJ,product/NN,reaction/NN,primary/NN,ll/VB,discuss/VB,hydroboration/JJ,oxidation/NN,reaction/NN,actually/RB,hydroboration/JJ,reaction/NN,follow/VB,completely/RB,separate/JJ,oxidation/NN,reaction/NN,hydroboration/NN,mechanism/NN,addition/NN,bh/NN,concerted/JJ,reaction/NN,bond/NN,break/VB,form/VB,time/NN,hydroboration/NN,happen/VB,syn/NN,addition/NN,boron/NN,hydrogen/NN,attach/VB,alkene/NN,time/NN,transition/NN,state/NN,center/NN,image/NN,produce/VB,sort/NN,box/NN,alkene/NN,carbon/NN,boron/NN,hydrogen/NN,final/JJ,step/NN,boron/NN,hydrogen/NN,remain/VB,attached/JJ,carbon/NN,hydrogen/NN,attach/VB,adjacent/JJ,carbon/NN,description/NN,fairly/RB,adequate/JJ,reaction/NN,actually/RB,continue/VB,happen/VB,bh/NN,continue/VB,react/VB,alkene/NN,bh/NN,end/VB,complex/NN,boron/JJ,atom/NN,attach/VB,alkyl/JJ,group/NN,trialkyl/NN,boron/NN,complex/NN,reaction/NN,produce/VB,product/NN,complex/NN,bh/NN,thf/NN,complex/NN,borane/NN,reality/NN,stable/JJ,bh/NN,boron/NN,configuration/NN,electron/NN,want/VB,natural/JJ,state/NN,actually/RB,create/VB,complex/VB,left/VB,furthermore/RB,instead/RB,bh/NN,complex/NN,tetrahydrofuran/NN,thf/RB,image/NN,right/NN,situation/NN,result/NN,reaction/NN,hydroboration/NN,oxidation/NN,hydroboration/NN,oxidation/NN,reaction/NN,reagent/NN,diborane/NN,bh/NN,alkene/NN,undergo/VB,hydroboration/NN,yield/VB,alkylboranes/JJ,oxidation/NN,alcohol/NN,reaction/NN,procedure/NN,simple/JJ,convenient/JJ,yield/NN,exceedingly/RB,high/JJ,product/NN,difficult/JJ,obtain/VB,alkene/NN,way/NN,diborane/NN,dimer/NN,hypothetical/JJ,bh/NN,borane/NN,reaction/NN,concern/NN,act/VB,bh/NN,tetrahydrofuran/NN,solvent/NN,hydroboration/NN,reagent/NN,exist/VB,monomer/NN,form/NN,acid/JJ,base/NN,complex/NN,solvent/JJ,hydroboration/NN,involve/VB,addition/NN,double/JJ,bond/NN,bh/NN,following/JJ,stage/NN,bh/NN,bhr/NN,hydrogen/NN,attach/VB,doubly/RB,bond/VB,carbon/NN,boron/NN,alkylborane/NN,undergo/JJ,oxidation/NN,boron/NN,replace/VB,stage/NN,reaction/NN,process/NN,hydroboration/JJ,oxidation/NN,permit/NN,effect/NN,addition/NN,carbon/NN,carbon/NN,double/JJ,bond/NN,element/NN,reaction/NN,carry/VB,ether/NN,commonly/RB,tetrahydrofuran/NN,diglyme/NN,diethylene/NN,glycol/NN,methyl/NN,ether/NN,ch/NN,diborane/NN,commercially/RB,available/JJ,tetrahydrofuran/NN,solution/NN,alkylborane/NN,isolate/VB,simply/RB,treat/VB,alkaline/JJ,hydrogen/NN,peroxide/NN,stereochemistry/NN,orientation/NN,hydroboration/NN,oxidation/NN,convert/VB,alkene/NN,alcohol/NN,addition/NN,highly/RB,regiospecific/VB,preferred/JJ,product/NN,exactly/RB,opposite/JJ,form/VB,oxymercuration/JJ,demercuration/NN,direct/JJ,acid/NN,catalyze/VB,hydration/NN,hydroboration/NN,oxtdation/NN,process/NN,product/NN,corresponding/JJ,markovnikov/JJ,addition/NN,water/NN,carbon/NN,carbon/NN,double/JJ,bond/NN,reaction/NN,dimethyl/JJ,butene/NN,illustrate/VB,particular/JJ,advantage/NN,method/NN,rearrangement/NN,occur/VB,hydroboration/NN,evidently/RB,carbonium/NN,ion/NN,intermediate/NN,method/NN,complication/NN,accompany/VB,addition/NN,reaction/NN,reaction/NN,illustrate/VB,stereochemistry/NN,synthesis/NN,hydroboration/NN,oxidation/NN,involve/VB,overall/JJ,syn/NN,addition/NN,oxymercuration/JJ,reduction/NN,oxymercuration/JJ,reduction/NN,propene/NN,alkene/NN,react/NN,mercuric/JJ,acetate/NN,presence/NN,water/NN,compound/NN,reduction/NN,yield/NN,alcohol/NN,stage/NN,oxymercuration/NN,involve/VB,addition/NN,carbon/NN,carbon/NN,double/JJ,bond/NN,hgoac/NN,reduction/NN,hgoac/NN,replace/VB,reaction/NN,sequence/NN,hydration/NN,alkene/NN,widely/RB,applicable/JJ,direct/JJ,hydration/NN,stage/NN,process/NN,oxymercuration/JJ,reduction/NN,fast/JJ,convenient/JJ,place/NN,mild/JJ,condition/NN,excellent/JJ,yield/NN,alkene/NN,add/VB,room/NN,temperature/NN,aqueous/JJ,solution/NN,mercuric/JJ,acetate/NN,dilute/VB,solvent/JJ,tetrahydrofuran/NN,reaction/NN,generally/RB,complete/VB,minute/NN,organomercurial/JJ,compound/NN,isolate/VB,simply/RB,reduce/VB,sodium/NN,borohydride/NN,nabh/RB,mercury/NN,re-cover/VB,ball/NN,elemental/JJ,mercury/NN,oxymercuration/NN,reduction/NN,highly/RB,regiospecific/JJ,alcohol/NN,corresponding/JJ,markovnikov/VB,addition/NN,water/NN,carbon/NN,carbon/NN,doublen/NN,bond/NN,oxymercuration/NN,involve/VB,electrophilic/JJ,addition/NN,carbon/NN,carbon/NN,double/JJ,bond/NN,mercuric/JJ,ion/NN,acting/NN,electrophile/RB,absence/NN,rearrangement/NN,high/JJ,degree/NN,typically/RB,oxymercuration/JJ,step/NN,argue/VB,open/JJ,carbonium/NN,ion/NN,intermediate/JJ,instead/RB,propose/VB,form/VB,cyclic/NN,mercurinium/NN,ion/NN,analogous/JJ,bromonium/NN,chloronium/NN,ion/NN,involved/JJ,addition/NN,halogen/NN,olah/JJ,report/VB,spectroscopic/NN,evidence/NN,preparation/NN,stable/JJ,solution/NN,mercurinium/NN,ion/NN,mercurinium/NN,ion/NN,attack/VB,nucleophilic/JJ,solvent/JJ,water/NN,present/JJ,case/NN,yield/VB,addition/NN,product/NN,attack/NN,prevent/VB,structural/JJ,feature/NN,net/JJ,result/NN,addition/NN,addition/NN,halogen/NN,attack/NN,sn/NN,type/NN,orientation/NN,addition/NN,nucleophile/RB,attach/VB,highly/RB,substituted/JJ,carbon/NN,free/JJ,carbonium/NN,ion/NN,intermediate/JJ,transition/NN,state/NN,reaction/NN,unstable/JJ,threemembered/JJ,ring/NN,sn/NN,character/NN,reduction/NN,generally/RB,stereospecific/JJ,certain/JJ,special/JJ,case/NN,accompany/VB,rearrangement/NN,stage/NN,overall/JJ,process/NN,general/NN,stereospecific/JJ,rearrangement/NN,occur/VB,common/JJ,reaction/NN,dimethyl/NN,butene/NN,illustrate/VB,absence/NN,rearrangement/NN,typical/JJ,intermediate/JJ,carbonium/NN,ion/NN,diel/NN,reaction/NN,diel/NN,reaction/NN,reaction/NN,specifically/RB,cycloaddition/NN,conjugate/VB,diene/NN,substituted/JJ,alkene/NN,commonly/RB,term/VB,dienophile/NN,form/VB,substituted/JJ,cyclohexene/NN,reaction/NN,proceed/VB,atom/NN,newly/RB,form/VB,ring/NN,carbon/NN,diel/NN,reaction/NN,reversible/JJ,decomposition/NN,reaction/NN,cyclic/JJ,retro/JJ,diel/NN,diel/NN,butadiene/NN,ethylene/NN,diel/NN,reaction/NN,generally/RB,consider/VB,useful/JJ,reaction/NN,organic/JJ,chemistry/NN,require/VB,little/JJ,energy/NN,create/VB,cyclohexene/NN,ring/NN,useful/JJ,organic/JJ,reaction/NN,concerted/JJ,single/JJ,step/NN,mechanism/NN,certainly/RB,involve/VB,new/JJ,carbon/NN,carbon/NN,bond/NN,partly/RB,form/VB,transition/NN,state/NN,necessarily/RB,extent/NN,diel/NN,reaction/NN,important/JJ,example/NN,cycloaddition/NN,reaction/NN,involve/VB,electron/NN,diene/NN,electron/NN,dienophile/NN,know/VB,cycloaddition/JJ,catalytic/JJ,addition/NN,hydrogen/NN,catalytic/JJ,hydrogenation/NN,alkene/NN,produce/VB,corresponding/JJ,alkane/NN,reaction/NN,carry/VB,pressure/NN,presence/NN,metallic/JJ,catalyst/NN,common/JJ,industrial/JJ,catalyst/NN,base/VB,platinum/NN,nickel/NN,palladium/NN,laboratory/NN,synthese/VB,raney/NN,nickel/VB,form/VB,alloy/NN,nickel/NN,aluminium/NN,employ/VB,catalytic/JJ,hydrogenation/NN,ethylene/NN,yield/VB,ethane/NN,proceed/NN,thusly/RB,ch/NN,ch/NN,catalyst/NN,ch/NN,ch/VB,electrophilic/JJ,addition/NN,addition/NN,reaction/NN,alkene/NN,follow/VB,mechanism/NN,electrophilic/JJ,addition/NN,example/NN,prin/NN,reaction/NN,electrophile/NN,carbonyl/NN,group/NN,halogenation/NN,addition/NN,elementary/JJ,bromine/NN,chlorine/NN,alkene/NN,yield/VB,vicinal/JJ,dibromo/NN,dichloroalkane/NN,respectively/RB,decoloration/NN,solution/NN,bromine/NN,water/NN,analytical/JJ,test/NN,presence/NN,alkene/NN,ch/VB,ch/NN,br/NN,brch/NN,ch/NN,reaction/NN,work/NN,high/JJ,electron/NN,density/NN,double/JJ,bond/NN,cause/VB,temporary/JJ,shift/NN,electron/NN,br/NN,br/NN,bond/NN,cause/VB,temporary/JJ,induced/JJ,dipole/JJ,br/NN,closest/JJ,double/JJ,bond/NN,slightly/RB,positive/JJ,electrophile/NN,addition/NN,hydrohalic/JJ,acid/NN,hcl/NN,hbr/JJ,alkene/NN,yield/VB,corresponding/JJ,haloalkane/NN,example/NN,type/NN,reaction/NN,ch/NN,ch/NN,ch/NN,hbr/NN,ch/NN,chbr/NN,ch/NN,carbon/NN,atom/NN,double/JJ,bond/NN,link/VB,different/JJ,number/NN,hydrogen/NN,atom/NN,halogen/NN,preferentially/RB,carbon/NN,hydrogen/NN,substituent/NN,markovnikov/VB,rule/NN,addition/NN,carbene/NN,carbenoid/JJ,yield/NN,corresponding/JJ,cyclopropane/NN,oxidation/NN,alkene/NN,oxidized/JJ,large/JJ,number/NN,oxidizing/JJ,agent/NN,presence/NN,oxygen/NN,alkene/NN,burn/VB,bright/JJ,flame/NN,carbon/NN,dioxide/NN,water/NN,catalytic/JJ,oxidation/NN,oxygen/NN,reaction/NN,percarboxylic/JJ,acid/NN,yield/NN,reaction/NN,ozone/NN,ozonolysis/NN,lead/VB,breaking/NN,double/JJ,bond/NN,yielding/NN,aldehyde/NN,ketone/VB,ch/NN,ch/NN,cho/JJ,cho/JJ,reaction/NN,determine/VB,position/NN,double/JJ,bond/NN,unknown/NN,alkene/NN,polymerization/NN,polymerization/NN,alkene/NN,economically/RB,important/JJ,reaction/NN,yield/NN,polymer/NN,high/JJ,industrial/JJ,value/NN,plastic/NN,polyethylene/NN,polypropylene/NN,polymerization/NN,proceed/VB,free/JJ,radical/JJ,ionic/JJ,mechanism/NN,substitution/NN,elimination/NN,reaction/NN,mechanism/NN,nucleophilic/JJ,substitution/NN,reaction/NN,nucleophilic/JJ,substitution/NN,reaction/NN,sn/NN,sn/NN,closely/RB,related/JJ,elimination/NN,reaction/NN,discuss/VB,later/RB,section/NN,generally/RB,good/JJ,idea/NN,learn/VB,reaction/NN,parallel/NN,reaction/NN,mechanism/NN,prefer/VB,substrate/NN,reaction/NN,compete/VB,important/JJ,understand/VB,substitution/NN,elimination/NN,reaction/NN,associate/VB,specific/JJ,compound/NN,mixture/NN,representation/NN,certain/JJ,reaction/NN,place/NN,time/NN,combination/NN,mechanism/NN,occur/VB,reaction/NN,compete/VB,influence/NN,solvent/JJ,nucleophile/JJ,choice/NN,determine/VB,factor/NN,reaction/NN,dominate/VB,note/NN,notation/NN,sn/NN,sn/VB,stand/VB,substitution/NN,place/NN,stand/VB,nucleophilic/NN,nucleophile/NN,displace/VB,nucleophile/RB,stand/VB,unimolecular/NN,concentration/NN,kind/NN,molecule/NN,determine/VB,rate/NN,reaction/NN,stand/VB,bimolecular/JJ,concentration/NN,type/NN,molecule/NN,determine/VB,rate/NN,reaction/NN,nucleophilic/JJ,substitution/NN,nucleophile/JJ,attack/NN,molecule/NN,place/NN,nucleophile/NN,leave/VB,nucleophile/NN,leave/VB,leave/VB,group/NN,nucleophilic/JJ,substitution/NN,require/VB,nucleophile/RB,lewis/JJ,base/NN,electrophile/NN,leave/VB,group/NN,leave/VB,group/NN,charged/JJ,neutral/JJ,moiety/NN,group/NN,break/VB,free/JJ,sn/NN,vs/NN,sn/VB,main/JJ,difference/NN,sn/NN,sn/NN,sn/NN,reaction/NN,step/NN,reaction/NN,initiate/VB,disassociation/NN,leave/VB,group/NN,sn/NN,reaction/NN,hand/NN,step/NN,reaction/NN,attacking/NN,nucleophile/RB,higher/JJ,affinity/NN,stronger/JJ,bond/VB,carbon/NN,force/VB,leave/VB,group/NN,leave/VB,thing/NN,happen/VB,single/JJ,step/NN,different/JJ,mechanism/NN,explain/VB,difference/NN,reaction/NN,rate/NN,sn/NN,sn/JJ,reaction/NN,sn/NN,reaction/NN,dependent/JJ,leave/VB,group/NN,disassociate/VB,carbon/NN,rate/NN,limit/VB,step/NN,reaction/NN,rate/NN,order/NN,reaction/NN,rate/NN,depend/VB,solely/RB,step/NN,alternatively/RB,sn/JJ,reaction/NN,single/JJ,step/NN,nucleophile/NN,come/VB,reactant/NN,opposite/JJ,leave/VB,group/NN,key/JJ,rate/NN,rate/NN,dependent/JJ,concentration/NN,nucleophile/RB,concentration/NN,reactant/NN,higher/JJ,concentration/NN,frequent/JJ,collision/NN,reaction/NN,rate/NN,second/JJ,order/NN,reaction/NN,nu/RB,attacking/NN,nucleophile/RB,sn/JJ,reaction/NN,primarily/RB,thing/NN,affect/VB,sn/NN,reaction/NN,place/NN,important/JJ,structure/NN,alkyl/NN,halide/NN,methyl/NN,primary/JJ,secondary/JJ,tertiary/JJ,carbon/NN,component/NN,determine/VB,sn/NN,reaction/NN,place/NN,nucleophilicity/NN,nucleophile/NN,solvent/JJ,reaction/NN,reactivity/NN,structure/NN,sn/NN,ch/NN,rch/NN,chx/NN,cx/VB,structure/NN,alkyl/NN,halide/NN,great/JJ,effect/NN,mechanism/NN,ch/VB,rch/NN,preferred/JJ,structure/NN,sn/NN,chx/NN,undergo/VB,sn/NN,proper/JJ,condition/NN,cx/NN,rarely/RB,involve/VB,sn/JJ,reaction/NN,nucleophilic/JJ,substitution/NN,bromine/NN,generic/JJ,reaction/NN,place/NN,nucleophile/NN,attacking/NN,opposite/JJ,bromine/JJ,atom/NN,notice/NN,bond/NN,point/VB,away/RB,bromine/NN,attacking/NN,nucleophile/RB,bond/NN,hydrogen/NN,bond/NN,little/RB,steric/JJ,hinderance/NN,approach/VB,nucleophile/RB,number/NN,group/NN,increase/NN,steric/NN,hinderance/NN,difficult/JJ,nucleophile/JJ,close/RB,carbon/NN,expel/VB,bromine/JJ,atom/NN,fact/NN,tertiary/JJ,carbon/NN,cx/NN,sterically/RB,hinder/VB,prevent/VB,sn/NN,mechanim/NN,place/NN,case/NN,example/NN,secondary/JJ,carbon/NN,great/JJ,deal/NN,steric/NN,hinderance/NN,sn/NN,mechanism/NN,happen/VB,depend/VB,entirely/RB,nucleophile/NN,solvent/JJ,sn/JJ,reaction/NN,prefer/VB,methyl/NN,halide/NN,primary/JJ,halide/NN,important/JJ,point/NN,mind/NN,clearly/RB,example/NN,sn/NN,reaction/NN,molecule/NN,undergo/VB,inversion/NN,bond/NN,attach/VB,carbon/NN,push/VB,away/RB,nucleophile/JJ,approach/NN,transition/NN,state/NN,bond/NN,planar/JJ,carbon/NN,bromine/NN,leave/VB,nucleophile/JJ,bond/NN,carbon/NN,bond/NN,fold/JJ,away/RB,nucleophile/RB,particularly/RB,important/JJ,chiral/JJ,pro/JJ,chiral/JJ,molecule/NN,configuration/NN,convert/VB,configuration/NN,vice/NN,versa/NN,ll/VB,contrast/NN,result/NN,sn/NN,reaction/NN,example/NN,ch/NN,cl/NN,ch/NN,cl/NN,nucleophile/RB,cl/NN,electrophile/NN,hoch/NN,product/NN,cl/NN,leave/VB,group/NN,ch/NN,br/NN,ch/NN,br/VB,reaction/NN,place/NN,acetone/NN,solvent/JJ,sodium/NN,iodide/NN,disassociate/VB,completely/RB,acetone/NN,leave/VB,iodide/NN,ion/NN,free/JJ,attack/VB,ch/NN,br/NN,molecule/NN,negatively/RB,charged/JJ,iodide/NN,ion/NN,nucleophile/JJ,attack/NN,methyl/NN,bromide/JJ,molecule/NN,force/VB,negatively/RB,charge/VB,bromide/JJ,ion/NN,place/NN,bromide/JJ,ion/NN,leave/VB,group/NN,nucleophilicity/NN,nucleophilicity/NN,rate/NN,nucleophile/NN,displace/VB,leave/VB,group/NN,reaction/NN,generally/RB,nucleophilicity/NN,stronger/JJ,larger/JJ,polarizable/JJ,stable/VB,nucleophile/RB,specific/JJ,number/NN,unit/NN,measure/NN,thing/NN,equal/JJ,nucleophile/NN,generally/RB,compare/VB,term/NN,relative/JJ,reactivity/NN,example/NN,particular/JJ,strong/JJ,nucleophile/RB,relative/JJ,reactivity/NN,particular/JJ,weak/JJ,nucleophile/NN,relationship/NN,generality/NN,thing/NN,solvent/JJ,substrate/NN,affect/VB,relative/JJ,rate/NN,generally/RB,good/JJ,guideline/NN,best/JJ,nucleophile/NN,nucleophile/NN,lewis/JJ,basis/NN,sn/JJ,reaction/NN,preferred/JJ,nucleophile/NN,strong/JJ,nucleophile/NN,weak/JJ,base/JJ,example/NN,rs/NN,br/NN,cn/NN,alternatively/RB,strong/JJ,nucleophile/NN,strong/JJ,base/NN,work/VB,mention/VB,earlier/RB,text/NN,reaction/NN,mechanism/NN,compete/JJ,case/NN,strong/JJ,nucleophile/NN,strong/JJ,sn/NN,mechanism/NN,compete/VB,mechanism/NN,example/NN,strong/JJ,nucleophile/NN,strong/JJ,basis/NN,include/VB,ro/NN,list/NN,descend/VB,nucleophilicity/NN,br/NN,cl/NN,seh/NN,leave/VB,group/NN,leave/VB,group/NN,group/NN,substrate/NN,leave/VB,case/NN,alkyl/NN,halide/NN,halide/JJ,ion/NN,leave/VB,carbon/NN,atom/NN,nucleophile/JJ,attack/NN,tendency/NN,nucleophile/JJ,leave/VB,relative/JJ,reactivity/NN,leave/VB,group/NN,br/NN,cl/NN,fluoride/NN,ion/NN,poor/JJ,leave/VB,group/NN,bond/NN,strongly/RB,rarely/RB,halide/JJ,substitution/NN,reaction/NN,reactivity/NN,leave/VB,group/NN,relate/VB,basicity/NN,stronger/JJ,basis/NN,poorer/NN,leave/VB,group/NN,solvent/JJ,solvent/JJ,play/VB,important/JJ,role/NN,sn/JJ,reaction/NN,particularly/RB,sn/NN,involve/VB,secondary/JJ,alkyl/NN,halide/NN,substrate/NN,determine/VB,factor/NN,mechanism/NN,solvent/JJ,great/JJ,effect/NN,reaction/NN,rate/NN,sn/NN,reaction/NN,sn/NN,mechanism/NN,prefer/VB,solvent/JJ,aprotic/JJ,polar/JJ,solvent/JJ,solvent/JJ,polar/JJ,polar/JJ,hydrogen/NN,polar/JJ,protic/JJ,solvent/NN,include/VB,water/NN,alcohol/NN,generally/RB,solvent/NN,polar/JJ,nh/NN,bond/NN,good/JJ,aprotic/JJ,polar/JJ,solvent/NN,hmpa/JJ,ch/NN,cn/NN,dmso/NN,dmf/VB,polar/JJ,solvent/JJ,prefer/VB,better/RB,allow/VB,dissociation/NN,halide/NN,alkyl/JJ,group/NN,protic/JJ,solvent/JJ,polar/JJ,hydrogen/NN,form/NN,cage/NN,hydrogen/NN,bond/VB,solvent/JJ,nucleophile/NN,hinder/VB,approach/NN,substrate/NN,relative/JJ,reactivity/NN,solvent/NN,hmpa/VB,ch/NN,cn/NN,dmf/NN,dmso/NN,sn/NN,reaction/NN,sn/NN,mechanism/NN,different/JJ,sn/NN,mechanism/NN,preference/NN,exactly/RB,opposite/JJ,case/NN,result/NN,reaction/NN,significantly/RB,different/JJ,sn/NN,mechanism/NN,structure/NN,play/VB,important/JJ,role/NN,sn/NN,mechanism/NN,role/NN,structure/NN,sn/NN,mechanism/NN,different/JJ,reactivity/NN,structure/NN,reversed/JJ,reactivity/NN,structure/NN,sn/NN,ch/NN,chx/NN,cx/VB,sn/NN,mechanism/NN,prefer/VB,tertiary/JJ,alkyl/NN,halide/NN,depend/VB,solvent/JJ,prefer/VB,secondary/JJ,alkyl/NN,halide/NN,sn/NN,mechanism/NN,operate/VB,primary/NN,halide/NN,methyl/NN,halide/NN,understand/VB,let/VB,look/NN,sn/NN,mechanism/NN,work/VB,nucleophilic/JJ,substitution/NN,generic/JJ,halide/NN,water/NN,molecule/NN,produce/VB,alcohol/NN,diagram/NN,step/NN,spontaneous/JJ,dissociation/NN,halide/NN,alkyl/NN,halide/NN,sn/NN,mechanism/NN,attacking/NN,nucleophile/NN,cause/VB,halide/JJ,leave/VB,sn/NN,mechanism/NN,depend/VB,ability/NN,halide/JJ,leave/VB,require/VB,certain/JJ,condition/NN,particular/JJ,stability/NN,carbocation/NN,crucial/JJ,ability/NN,halide/JJ,leave/VB,know/VB,tertiary/JJ,carbocation/NN,stable/JJ,best/JJ,candidate/NN,sn/NN,mechanism/NN,appropriate/JJ,condition/NN,secondary/JJ,carbocation/NN,operate/VB,sn/NN,mechanism/NN,primary/NN,methyl/NN,carbocation/NN,stable/JJ,allow/VB,mechanism/NN,happen/VB,halide/NN,dissociate/VB,water/NN,act/NN,nucleophile/JJ,bond/NN,carbocation/NN,sn/NN,reaction/NN,inversion/NN,cause/VB,nucleophile/NN,attacking/NN,opposite/JJ,halide/NN,bond/VB,carbon/NN,sn/NN,mechanism/NN,halide/NN,left/VB,bond/NN,carbon/NN,planar/JJ,water/NN,molecule/NN,free/JJ,attack/VB,result/NN,primarily/RB,racemic/JJ,mixture/NN,final/JJ,step/NN,hydrogen/NN,bond/VB,water/NN,molecule/NN,attack/VB,water/NN,molecule/NN,leave/VB,alcohol/NN,note/NN,racemic/JJ,mixture/NN,imply/RB,entirely/RB,equal/JJ,mixture/NN,rarely/RB,case/NN,sn/NN,slight/JJ,tendency/NN,attack/NN,opposite/JJ,halide/NN,result/NN,steric/NN,hinderence/NN,leave/VB,halide/NN,close/RB,leave/VB,block/VB,nucleophile/RB,approach/NN,solvent/JJ,sn/NN,mechanism/NN,sn/NN,affect/VB,solvent/JJ,structure/NN,reason/NN,differ/NN,sn/NN,mechanism/NN,polar/JJ,protic/JJ,solvent/JJ,polarity/NN,solvent/JJ,associate/VB,dielectric/JJ,constant/JJ,solvent/JJ,solution/NN,high/JJ,dielectric/JJ,constant/NN,better/RB,able/JJ,support/VB,separated/JJ,ion/NN,solution/NN,sn/JJ,reaction/NN,concern/VB,polar/JJ,hydrogen/NN,atom/NN,cage/VB,nucleophile/NN,happen/VB,polar/JJ,protic/JJ,solvent/JJ,sn/JJ,reaction/NN,worry/VB,mind/NN,mechanism/NN,reaction/NN,step/NN,importantly/RB,rate/NN,limit/VB,step/NN,sn/NN,reaction/NN,ability/NN,create/VB,stable/NN,carbocation/NN,halide/JJ,anion/NN,leave/VB,polar/JJ,protic/JJ,solvent/JJ,polar/JJ,aprotic/JJ,solvent/JJ,create/VB,stable/NN,cation/NN,polar/JJ,hydrogen/NN,stabilize/VB,halide/JJ,anion/NN,better/RB,able/JJ,leave/VB,improve/VB,rate/NN,limit/VB,step/NN,goal/NN,cage/VB,nucleophile/NN,unrelated/JJ,rate/NN,limit/VB,step/NN,cage/VB,state/NN,second/JJ,step/NN,attack/NN,nucleophile/NN,faster/JJ,step/NN,caging/NN,simply/RB,ignore/VB,summary/NN,sn/NN,sn/NN,reaction/NN,mechanism/NN,reaction/NN,mechanism/NN,number/NN,different/JJ,reaction/NN,usually/RB,organic/JJ,chemistry/NN,goal/NN,synthesize/VB,product/NN,case/NN,possibly/RB,compete/VB,mechanism/NN,particularly/RB,case/NN,sn/NN,reaction/NN,compete/VB,dominating/JJ,mechanism/NN,decide/VB,product/NN,know/VB,mechanism/NN,condition/NN,favor/VB,determine/VB,product/NN,case/NN,know/VB,mechanism/NN,allow/VB,set/VB,environment/NN,favorable/JJ,mechanism/NN,mean/VB,difference/NN,product/NN,minute/NN,ice/NN,age/NN,design/VB,synthesis/NN,product/NN,need/VB,consider/VB,want/VB,product/NN,option/NN,know/VB,option/NN,ve/NN,decide/VB,reaction/NN,need/VB,consider/VB,mechanism/NN,reaction/NN,ask/VB,create/JJ,condition/NN,happen/VB,correctly/RB,happen/VB,quickly/RB,elimination/NN,reaction/NN,nucleophilic/JJ,substitution/NN,reaction/NN,elimination/NN,reaction/NN,share/NN,lot/NN,common/JJ,characteristic/NN,sn/NN,sn/JJ,reaction/NN,compete/JJ,product/NN,different/JJ,important/JJ,understand/VB,understand/VB,kind/NN,mechanism/NN,difficult/JJ,product/NN,desire/NN,reaction/NN,addition/NN,sn/NN,sn/JJ,reaction/NN,reference/VB,bit/NN,way/NN,comparison/NN,contrast/NN,probably/RB,best/VB,read/VB,section/NN,continue/VB,elimination/NN,reaction/NN,mechanism/NN,create/VB,alkene/JJ,product/NN,haloalkane/JJ,reactant/NN,elimination/NN,sn/NN,sn/NN,substitution/NN,mechanism/NN,occur/VB,methyl/NN,halide/NN,reaction/NN,create/VB,double/JJ,bond/NN,carbon/NN,atom/NN,methylhalide/NN,carbon/NN,note/NN,notation/NN,stand/VB,elimination/NN,stand/VB,unimolecular/NN,concentration/NN,kind/NN,molecule/NN,determine/VB,rate/NN,reaction/NN,stand/VB,bimolecular/JJ,concentration/NN,type/NN,molecule/NN,determine/VB,rate/NN,reaction/NN,vs/NN,reaction/NN,rate/NN,different/JJ,pathway/NN,create/VB,alkene/NN,haloalkane/NN,sn/NN,sn/JJ,reaction/NN,key/JJ,difference/NN,reaction/NN,rate/NN,provide/VB,great/JJ,insight/NN,mechanism/NN,reaction/NN,sn/NN,reaction/NN,step/JJ,reaction/NN,like/VB,sn/JJ,reaction/NN,rate/NN,limit/VB,step/NN,dissociation/NN,halide/NN,alkane/NN,order/NN,reaction/NN,depend/VB,concentration/NN,haloalkane/NN,reaction/NN,rate/NN,hand/NN,reaction/NN,sn/NN,reaction/NN,step/JJ,reaction/NN,sn/JJ,reaction/NN,rate/NN,limit/VB,step/NN,ability/NN,nucleophile/JJ,attach/VB,alkane/NN,displace/VB,halide/NN,second/JJ,order/NN,reaction/NN,depend/VB,concentration/NN,nucleophile/NN,haloalkane/NN,reaction/NN,rate/NN,nu/RB,attacking/NN,nucleophile/RB,zaitsev/VB,rule/NN,zaitsev/NN,rule/NN,spel/VB,saytzeff/NN,state/NN,elimination/NN,reaction/NN,multiple/JJ,product/NN,possible/JJ,stable/JJ,alkene/NN,major/JJ,product/NN,highly/RB,substitute/VB,alkene/NN,hydrogen/NN,substituent/NN,major/JJ,product/NN,reaction/NN,produce/VB,mixture/NN,product/NN,possible/JJ,generally/RB,follow/JJ,zaitsev/NN,rule/NN,ll/VB,reaction/NN,follow/VB,zaitsev/VB,rule/NN,reliably/RB,tend/VB,produce/VB,purer/NN,product/NN,reaction/NN,bromo/VB,methylbutane/NN,image/NN,represent/VB,possible/JJ,pathway/NN,bromo/VB,methylbutane/NN,potential/JJ,product/NN,ene/NN,ene/VB,image/NN,right/JJ,simplified/JJ,drawing/NN,molecular/JJ,product/NN,image/NN,center/NN,left/VB,bromine/NN,second/JJ,carbon/NN,reaction/NN,hydrogen/NN,remove/VB,st/NN,rd/JJ,carbon/NN,zaitsev/NN,rule/NN,hydrogen/NN,remove/VB,predominantly/RB,rd/JJ,carbon/NN,reality/NN,mixture/NN,product/NN,ene/NN,mechanism/NN,reaction/NN,ll/VB,later/RB,necessarily/RB,case/NN,reactivity/NN,structure/NN,rch/NN,chx/NN,cx/VB,mechanism/NN,concerted/JJ,higly/RB,stereospecific/JJ,occur/VB,leave/VB,group/NN,coplanar/NN,position/NN,newman/NN,projection/NN,configuration/NN,behaviour/NN,stem/VB,best/JJ,overlap/NN,orbital/NN,adjacent/JJ,carbon/NN,pi/NN,bond/NN,form/VB,leave/VB,group/NN,bring/VB,position/NN,structure/NN,molecule/NN,mechanism/NN,place/NN,mechanism/NN,elimination/NN,note/VB,coplanarity/NN,atom/NN,molecule/NN,accessible/JJ,coplanar/NN,conformation/NN,react/VB,route/NN,furthermore/RB,mechanism/NN,operate/VB,contrary/JJ,zaitsev/VB,rule/NN,coplanar/NN,hydrogen/NN,leave/VB,group/NN,result/NN,stable/NN,alkene/VB,good/JJ,example/NN,happen/VB,look/VB,cyclohexane/NN,cyclohexene/NN,derivative/NN,operate/VB,condition/NN,preferential/JJ,elimination/NN,let/VB,look/VB,example/NN,reactant/NN,chloro/JJ,drawing/NN,left/VB,conformation/NN,drawing/NN,ring/NN,flip/NN,center/NN,newman/JJ,projection/NN,conformation/NN,drawing/NN,right/RB,product/NN,assume/VB,treat/VB,chloro/NN,strong/JJ,base/NN,example/NN,ch/NN,ch/NN,ethanolate/NN,mechanism/NN,dominate/VB,hydrogen/NN,carbon/NN,adjacent/JJ,chlorinated/JJ,carbon/NN,red/JJ,green/JJ,hard/JJ,attach/VB,carbon/NN,red/JJ,hydrogen/NN,angle/VB,little/JJ,plane/NN,viewer/NN,red/JJ,hydrogen/NN,hydrogen/NN,chlorine/NN,atom/NN,eligible/NN,mechanism/NN,product/NN,ene/NN,notice/NN,contrary/JJ,zaitsev/VB,rule/NN,substituted/JJ,alkene/NN,prefer/VB,rule/NN,primary/JJ,product/NN,leave/VB,substituted/JJ,alkene/NN,simply/RB,produce/VB,steric/JJ,hindrance/NN,image/NN,molecule/NN,ring/NN,flip/NN,conformation/NN,product/NN,possible/JJ,newman/NN,projection/NN,hydrogen/NN,chlorine/NN,atom/NN,important/JJ,consider/VB,mechanism/NN,understand/VB,geometry/NN,molecule/NN,geometry/NN,advantage/NN,preferentially/RB,single/JJ,product/NN,time/NN,prevent/VB,product/NN,want/VB,ll/VB,need/RB,consider/VB,different/JJ,mechanism/NN,product/NN,note/NN,word/NN,periplanar/NN,instead/RB,coplanar/NN,coplanar/NN,imply/VB,precisely/RB,degree/NN,separation/NN,peri/NN,greek/NN,near/NN,imply/VB,degree/NN,periplanar/NN,actually/RB,accurate/JJ,case/NN,chloro/NN,example/NN,molecular/JJ,force/NN,chlorine/NN,atom/NN,actually/RB,slightly/RB,degree/NN,hydrogen/NN,isopropyl/JJ,group/NN,case/NN,periplanar/NN,correct/JJ,term/NN,elimination/NN,alkyl/NN,halide/NN,base/NN,mechanism/NN,begin/VB,dissociation/NN,leave/VB,group/NN,alkyl/NN,produce/VB,carbocation/NN,alkyl/JJ,group/NN,leave/VB,anion/NN,way/NN,sn/NN,reaction/NN,begin/VB,thing/NN,help/VB,initiate/VB,step/NN,sn/JJ,reaction/NN,help/NN,initiate/VB,step/NN,reaction/NN,specifically/RB,secondary/JJ,tertiary/JJ,carbocation/NN,prefer/VB,stable/JJ,primary/NN,carbocation/VB,choice/NN,solvent/JJ,sn/NN,polar/JJ,protic/JJ,solvent/JJ,prefer/VB,polar/JJ,aspect/NN,stabilize/VB,carbocation/NN,protic/JJ,aspect/NN,stabilize/VB,anion/NN,difference/NN,reaction/NN,sn/NN,pathway/NN,depend/VB,second/JJ,step/NN,action/NN,nucleophile/NN,sn/JJ,reaction/NN,strong/JJ,nucleophile/NN,weak/JJ,base/NN,prefer/VB,nucleophile/RB,attack/NN,bond/NN,carbocation/NN,reaction/NN,strong/JJ,nucleophile/NN,prefer/VB,difference/NN,strong/JJ,nucleophile/NN,strong/JJ,base/NN,cause/VB,nucleophile/JJ,attack/VB,hydrogen/NN,carbon/NN,instead/RB,carbocation/NN,nucleophile/JJ,base/NN,extract/NN,hydrogen/NN,cause/VB,bond/VB,electron/NN,fall/VB,produce/VB,pi/NN,bond/NN,carbocation/NN,hydrogen/NN,leave/VB,group/NN,lose/VB,separate/JJ,step/NN,fact/NN,requirement/NN,geometry/NN,mechanism/NN,reliably/RB,produce/VB,product/NN,follow/VB,zaitsev/VB,rule/NN,reference/NN
10

Organic Chemistry/Chirality
introduction/NN,chirality/VB,pronounced/JJ,kie/NN,ral/JJ,tee/NN,property/NN,handedness/NN,attempt/VB,superimpose/VB,right/JJ,hand/NN,left/VB,match/VB,sense/NN,right/JJ,hand/NN,thumb/NN,overlay/VB,left/JJ,hand/NN,pinky/NN,finger/NN,hand/NN,superimpose/VB,identically/RB,fact/NN,finger/NN,hand/NN,connect/VB,way/NN,object/NN,property/NN,include/VB,molecule/NN,object/NN,chiral/JJ,object/NN,superimpose/VB,mirror/NN,image/NN,chiral/JJ,object/NN,plane/NN,symmetry/NN,achiral/JJ,object/NN,plane/NN,symmetry/NN,rotation/NN,reflection/NN,axis/NN,reflection/NN,rotate/VB,version/NN,optical/JJ,isomer/NN,enantiomer/NN,stereoisomer/NN,exhibit/RB,chirality/JJ,optical/JJ,isomerism/NN,application/NN,inorganic/JJ,chemistry/NN,organic/JJ,chemistry/NN,physical/JJ,chemistry/NN,pharmacology/NN,biochemistry/NN,form/VB,asymmetric/JJ,center/NN,present/JJ,example/NN,carbon/NN,different/JJ,group/NN,bond/VB,stereocenter/NN,enantiomer/NN,opposite/JJ,configuration/NN,molecule/NN,source/NN,asymmetry/NN,optical/JJ,isomer/NN,perfect/JJ,reflection/NN,superimposeable/JJ,stereocenter/NN,invert/VB,molecule/NN,example/NN,diastereomer/NN,enantiomer/NN,diastereomer/NN,seldom/RB,physical/JJ,property/NN,stereocentre/NN,symmetrical/JJ,cause/VB,situation/NN,chiral/JJ,centre/NN,present/JJ,isomer/NN,result/VB,compound/NN,meso/NN,compound/NN,chiral/JJ,relationship/NN,mixture/NN,equal/JJ,enantiomer/NN,racemic/JJ,mixture/NN,symmetry/NN,molecule/NN,object/NN,determine/VB,chiral/JJ,technically/RB,molecule/NN,achiral/JJ,chiral/JJ,axis/NN,improper/JJ,rotation/NN,fold/JJ,rotation/NN,rotation/NN,follow/VB,reflection/NN,plane/NN,perpendicular/JJ,axis/NN,map/NN,molecule/NN,chiral/JJ,molecule/NN,necessarily/RB,dissymmetric/JJ,completely/RB,devoid/JJ,symmetry/NN,rotational/JJ,symmetry/NN,simplified/JJ,rule/NN,apply/VB,tetrahedrally/RB,bond/VB,carbon/NN,illustration/NN,substituent/NN,different/JJ,molecule/NN,chiral/JJ,important/JJ,mind/NN,molecule/NN,dissolve/VB,solution/NN,gas/NN,phase/NN,usually/RB,considerable/JJ,flexibility/NN,adopt/VB,variety/NN,different/JJ,conformation/NN,conformation/NN,chiral/JJ,assess/VB,chirality/NN,use/VB,structural/JJ,picture/NN,molecule/NN,correspond/VB,chemical/NN,conformation/NN,lowest/JJ,energy/NN,chiral/JJ,compound/NN,stereocenter/NN,commonly/RB,chiral/JJ,molecule/NN,point/NN,chirality/NN,center/VB,single/JJ,atom/NN,usually/RB,carbon/NN,different/JJ,substituent/NN,enantiomer/NN,compound/NN,different/JJ,absolute/JJ,configuration/NN,center/NN,center/NN,stereogenic/VB,grouping/NN,molecular/JJ,entity/NN,consider/VB,focus/NN,stereoisomerism/NN,exemplify/VB,carbon/NN,amino/JJ,acid/NN,special/JJ,nature/NN,carbon/NN,ability/NN,form/VB,bond/NN,different/JJ,substituent/NN,mean/VB,mirror/NN,image/NN,carbon/NN,different/JJ,bond/NN,original/JJ,compound/NN,matter/NN,try/VB,rotate/VB,understand/VB,vital/JJ,goal/NN,organic/JJ,chemistry/NN,understand/VB,use/VB,tool/NN,synthesize/VB,compound/NN,desire/VB,chirality/NN,different/JJ,arrangement/NN,effect/NN,undesired/JJ,carbon/NN,atom/NN,chiral/JJ,different/JJ,item/NN,bond/VB,time/NN,refer/VB,carbon/NN,heteroatom/NN,hydrogen/NN,heteroatom/NN,bond/NN,carbon/NN,bond/NN,hydrogen/NN,atom/NN,refer/VB,nitrogen/NN,atom/NN,bond/VB,different/JJ,type/NN,molecule/NN,nitrogen/NN,atom/NN,utilize/VB,lone/JJ,pair/NN,nucleophile/RB,nitrogen/NN,bond/NN,chiral/JJ,lone/JJ,pair/NN,electron/NN,flip/VB,atom/NN,spontaneously/RB,atom/NN,organic/JJ,molecule/NN,bond/VB,different/JJ,type/NN,atom/NN,chain/NN,atom/NN,consider/VB,chiral/JJ,carbon/NN,atom/NN,type/NN,atom/NN,different/JJ,substituent/NN,carbon/NN,atom/NN,form/NN,chiral/JJ,center/NN,know/VB,stereocenter/NN,chiral/JJ,molecule/NN,stereocenter/NN,draw/VB,molecule/NN,stereocenter/NN,usually/RB,indicate/VB,asterisk/NN,carbon/NN,example/NN,indicated/JJ,carbon/NN,atom/NN,stereocenter/NN,left/VB,carbon/NN,atom/NN,cl/NN,br/NN,ch/VB,different/JJ,substituent/NN,mean/VB,stereocenter/JJ,center/NN,carbon/NN,atom/NN,ethyl/NN,group/NN,ch/NN,ch/VB,methyl/NN,group/NN,ch/NN,stereocenter/NN,right/RB,carbon/NN,atom/NN,cl/NN,look/VB,ring/NN,double/JJ,bond/NN,mean/VB,substituent/NN,carbon/NN,different/JJ,different/JJ,substituent/NN,carbon/NN,stereocenter/NN,molecule/NN,chiral/JJ,molecule/NN,multiple/JJ,chiral/JJ,center/NN,chiral/JJ,overall/JJ,meso/JJ,compound/NN,occur/VB,symmetry/NN,element/NN,mirror/NN,plane/NN,inversion/NN,center/NN,relate/VB,chiral/JJ,center/NN,fischer/JJ,projection/NN,fischer/JJ,projection/NN,german/NN,chemist/NN,hermann/NN,emil/NN,fischer/NN,ingenious/JJ,means/NN,represent/VB,configuration/NN,carbon/NN,atom/NN,consideration/NN,carbon/NN,center/NN,place/NN,horizontally/RB,bond/NN,extend/VB,observer/NN,backward/RB,bond/NN,vertical/JJ,position/NN,shorthanded/JJ,line/NN,horizontal/JJ,forward/NN,vertical/JJ,figure/NN,principle/NN,fischer/JJ,projection/NN,operation/NN,fischer/JJ,projection/NN,fischer/JJ,projection/NN,exchange/NN,substituent/NN,position/NN,result/NN,inversion/NN,stereocenter/JJ,rotation/NN,fischer/JJ,projection/NN,result/NN,inversion/NN,rotation/NN,fischer/JJ,projection/NN,preserve/VB,configuration/NN,naming/NN,convention/NN,main/JJ,configuration/NN,oldest/JJ,relative/JJ,use/NN,deprecate/VB,current/JJ,absolute/JJ,relative/JJ,configuration/NN,description/NN,mainly/RB,glycochemistry/NN,configuration/NN,assign/VB,purely/RB,empirical/JJ,basis/NN,optical/JJ,activity/NN,optical/JJ,activity/NN,optical/JJ,isomer/NN,direction/NN,rotate/VB,plane/NN,polarize/VB,light/NN,isomer/NN,rotate/VB,plane/NN,clockwise/RB,viewer/NN,light/NN,travele/VB,isomer/NN,labele/VB,counterpart/NN,labele/VB,isomer/NN,term/VB,respectively/RB,dextrorotatory/NN,levorotatory/NN,labele/VB,easy/JJ,confuse/VB,encourage/VB,iupac/NN,fact/NN,enantiomer/NN,rotate/VB,polarised/JJ,light/NN,clockwise/RB,enantiomer/NN,relate/VB,relative/JJ,configuration/NN,relative/JJ,configuration/NN,fischer/NN,research/NN,carbohydrate/NN,chemistry/NN,glyceraldehyde/VB,simplest/JJ,sugar/NN,systematic/JJ,template/NN,chiral/JJ,molecule/NN,denote/VB,possible/JJ,configuration/NN,rotate/VB,polarised/JJ,light/NN,clockwise/RB,respectively/RB,glycerladehyde/VB,start/VB,molecule/NN,relative/JJ,configuration/NN,assignent/NN,molecule/NN,assign/VB,configuration/NN,chiral/JJ,centre/NN,formally/RB,obtain/VB,glyceraldehyde/NN,substitution/NN,reason/NN,naming/NN,scheme/NN,relative/JJ,configuration/NN,glyceraldehyde/NN,glyceraldehyde/NN,glyceraldehyde/NN,glyceraldehyde/NN,glyceraldehyde/VB,optical/JJ,isomer/NN,spatial/JJ,configuration/NN,atom/NN,relate/VB,molecule/NN,glyceraldehyde/VB,glyceraldehyde/NN,chiral/JJ,isomer/NN,labele/VB,certain/JJ,chemical/NN,manipulation/NN,perform/VB,glyceraldehyde/NN,affect/VB,configuration/NN,historical/JJ,use/NN,purpose/NN,possibly/RB,combine/VB,convenience/NN,smallest/JJ,commonly/RB,chiral/JJ,molecule/NN,result/VB,use/NN,nomenclature/NN,compound/NN,analogy/NN,glyceraldehyde/VB,generally/RB,produce/VB,unambiguous/JJ,designation/NN,easiest/JJ,small/JJ,biomolecule/NN,similar/JJ,glyceraldehyde/VB,optical/JJ,isomer/NN,example/NN,amino/JJ,acid/NN,alanine/NN,alanine/NN,optical/JJ,isomer/NN,labele/VB,accord/VB,isomer/NN,glyceraldehyde/NN,come/VB,glycine/NN,amino/JJ,acid/NN,derive/VB,glyceraldehyde/NN,incidentally/RB,retain/VB,optical/JJ,activity/NN,central/JJ,carbon/NN,chiral/JJ,alanine/NN,essentially/RB,methylated/JJ,glycine/NN,optical/JJ,activity/NN,labele/VB,unrelated/JJ,indicate/NN,enantiomer/NN,dextrorotatory/JJ,levorotatory/JJ,compound/NN,stereochemistry/NN,relate/VB,dextrorotatory/NN,levorotatory/JJ,enantiomer/NN,glyceraldehyde/NN,amino/JJ,acid/NN,commonly/RB,protein/NN,dextrorotatory/JJ,wavelength/NN,nm/NN,fructose/NN,refer/VB,levulose/RB,levorotatory/JJ,dextrorotatory/JJ,isomer/NN,glyceraldehyde/NN,fact/NN,isomer/NN,lucky/JJ,guess/NN,time/NN,establish/VB,way/NN,tell/VB,configuration/NN,dextrorotatory/JJ,guess/NN,turn/VB,wrong/JJ,labele/VB,situation/NN,confuse/VB,rule/NN,thumb/NN,determine/VB,isomeric/JJ,form/NN,amino/JJ,acid/NN,corn/NN,rule/NN,group/NN,cooh/JJ,nh/NN,unnamed/JJ,carbon/NN,chain/NN,arrange/VB,chiral/JJ,center/NN,carbon/NN,atom/NN,group/NN,arrange/VB,clockwise/RB,carbon/NN,atom/NN,form/NN,counter/JJ,clockwise/RB,form/NN,rule/NN,hold/VB,hydrogen/NN,atom/NN,point/VB,page/NN,absolute/JJ,configuration/NN,main/JJ,article/NN,absolute/JJ,configuration/NN,stem/VB,cahn/NN,ingold/NN,prelog/NN,priority/NN,rule/NN,allow/VB,precise/JJ,description/NN,stereocenter/NN,reference/NN,compound/NN,fact/NN,basis/NN,atomic/JJ,number/NN,stereocenter/NN,substituent/VB,way/NN,optical/JJ,isomer/NN,configuration/NN,involve/VB,reference/NN,molecule/NN,glyceraldehyde/NN,label/VB,chiral/JJ,center/NN,accord/VB,ligand/NN,assign/VB,priority/NN,accord/VB,cahn/NN,ingold/NN,prelog/NN,priority/NN,rule/NN,base/VB,atomic/JJ,number/NN,label/VB,chiral/JJ,center/NN,molecule/NN,extension/NN,chiral/JJ,molecule/NN,involve/VB,chiral/JJ,center/NN,greater/JJ,generality/NN,label/VB,example/NN,isomer/NN,versu/VB,diastereomer/NN,fixed/JJ,relation/NN,isomer/NN,dextrorotatory/JJ,levorotatory/JJ,depend/VB,exact/JJ,ligand/NN,fixed/JJ,relation/NN,example/NN,glyceraldehyde/NN,ligand/NN,hydroxy/JJ,group/NN,thiol/NN,group/NN,sh/NN,swap/VB,labele/VB,definition/NN,affect/VB,substitution/NN,substitution/NN,invert/VB,molecule/NN,labele/VB,fact/NN,sulfur/NN,atomic/JJ,number/NN,higher/JJ,carbon/NN,oxygen/NN,lower/JJ,note/NN,incorrect/JJ,oxygen/NN,higher/JJ,atomic/JJ,number/NN,carbon/NN,sulfur/NN,higher/JJ,atomic/JJ,number/NN,oxygen/NN,reason/NN,assignment/NN,priority/NN,change/VB,example/NN,ch/NN,sh/NN,group/NN,higher/JJ,priority/NN,cho/NN,glyceraldehyde/NN,cho/NN,priority/NN,ch/NN,reason/NN,remain/VB,common/JJ,use/NN,certain/JJ,area/NN,amino/JJ,acid/NN,carbohydrate/NN,chemistry/NN,convenient/JJ,common/JJ,amino/JJ,acid/NN,higher/JJ,organism/NN,labele/VB,way/NN,conversely/RB,cysteine/NN,example/NN,sulfur/NN,higher/JJ,atomic/JJ,number/NN,word/NN,racemic/JJ,derive/VB,latin/NN,word/NN,grape/NN,term/NN,origin/NN,work/NN,louis/NN,pasteur/NN,isolate/VB,racemic/JJ,tartaric/NN,acid/NN,wine/NN,chiral/JJ,compound/NN,stereocenter/NN,possible/JJ,molecule/NN,chiral/JJ,actual/JJ,point/NN,chirality/NN,stereocenter/NN,commonly/RB,encounter/VB,example/NN,include/VB,naphthol/NN,binol/NN,dichloro/NN,allene/NN,axial/JJ,chirality/NN,cyclooctene/NN,planar/JJ,chirality/NN,example/NN,isomer/NN,following/JJ,figure/NN,different/JJ,isomer/NN,convert/VB,spontaneously/RB,restriction/NN,rotation/NN,double/JJ,bond/NN,image/NN,hexa/NN,dien/NN,ol/JJ,png/NN,type/NN,chiral/JJ,compound/NN,stereocenter/NN,restriction/NN,rotation/NN,single/JJ,bond/NN,steric/JJ,hindrance/NN,exist/VB,consider/VB,following/JJ,example/NN,binol/JJ,molecule/NN,px/VB,px/VB,biphenyl/NN,bond/NN,rotate/VB,group/NN,cause/VB,steric/JJ,hindrance/NN,px/NN,compound/NN,exhibit/VB,spiral/NN,chirality/NN,property/NN,optical/JJ,isomer/NN,enantiomer/NN,present/NN,symmetric/JJ,environment/NN,identical/JJ,chemical/NN,physical/JJ,property/NN,ability/NN,rotate/VB,plane/NN,polarize/VB,light/NN,equal/JJ,opposite/JJ,direction/NN,solution/NN,equal/JJ,optically/RB,active/JJ,isomer/NN,enantiomer/NN,know/VB,racemic/JJ,solution/NN,net/JJ,rotation/NN,plane/NN,polarize/VB,light/NN,enantiomer/NN,differ/VB,interact/VB,different/JJ,optical/JJ,isomer/NN,compound/NN,nature/NN,biological/JJ,compound/NN,amino/JJ,acid/NN,occur/VB,single/JJ,enantiomer/NN,result/JJ,different/JJ,enantiomer/NN,compound/NN,substantially/RB,different/JJ,biological/JJ,effect/NN,different/JJ,enantiomer/NN,chiral/JJ,drug/NN,different/JJ,pharmological/JJ,effect/NN,mainly/RB,protein/NN,bind/NN,chiral/JJ,example/NN,spearmint/NN,leave/VB,caraway/JJ,seed/NN,respectively/RB,contain/JJ,carvone/NN,carvone/NN,enantiomer/NN,carvone/NN,smell/RB,different/JJ,person/NN,taste/NN,receptor/NN,contain/VB,chiral/JJ,molecule/NN,behave/VB,differently/RB,presence/NN,different/JJ,enantiomer/NN,limonene/VB,enantiomer/NN,different/JJ,smell/VB,form/NN,amino/JJ,acid/NN,tend/VB,taste/VB,sweet/JJ,form/NN,usually/RB,tasteless/JJ,chiral/JJ,taste/NN,molecule/NN,smell/VB,orange/NN,lemon/NN,example/NN,enantiomer/NN,penicillin/NN,activity/NN,stereoselective/NN,antibiotic/JJ,work/NN,peptide/NN,link/NN,alanine/NN,occur/VB,cell/NN,wall/NN,bacterium/NN,human/NN,antibiotic/JJ,kill/VB,bacterium/NN,amino/JJ,acid/NN,electric/JJ,magnetic/JJ,field/NN,polarize/VB,light/NN,oscillate/NN,geometric/JJ,plane/NN,axis/NN,normal/JJ,plane/NN,direction/NN,energy/NN,propagation/NN,optically/RB,active/JJ,isomer/NN,rotate/VB,plane/NN,field/NN,oscillate/JJ,polarize/VB,light/NN,actually/RB,rotate/VB,racemic/JJ,mixture/NN,rotate/VB,left/VB,enantiomer/NN,right/NN,cancel/VB,net/NN,rotation/NN,chirality/NN,biology/NN,biologically/RB,active/JJ,molecule/NN,chiral/JJ,include/VB,naturally/RB,occur/VB,amino/JJ,acid/NN,building/JJ,block/NN,protein/NN,sugar/NN,interestingly/RB,biological/JJ,compound/NN,chirality/NN,amino/JJ,acid/NN,sugar/NN,origin/NN,homochirality/NN,biology/NN,subject/NN,debate/NN,enantiomer/NN,amino/JJ,acid/NN,chiral/JJ,object/NN,different/JJ,interaction/NN,enantiomer/NN,chiral/JJ,object/NN,enzyme/NN,chiral/JJ,distinguish/VB,enantiomer/NN,chiral/JJ,substrate/NN,imagine/VB,enzyme/NN,glove/NN,cavity/NN,bound/VB,substrate/NN,glove/NN,right/RB,hand/VB,enantiomer/NN,fit/VB,inside/NN,bound/VB,enantiomer/NN,poor/JJ,fit/NN,unlikely/JJ,bind/NN,chirality/NN,inorganic/JJ,chemistry/NN,image/NN,delta/JJ,ruthenium/NN,tri/NN,bipyridine/NN,cation/NN,ball/NN,png/JJ,thumb/NN,ru/NN,coordination/NN,compound/NN,chiral/JJ,example/NN,know/VB,ru/NN,bipyridine/NN,complex/NN,ligand/NN,adopt/VB,chiral/JJ,propeller/NN,arrangement/NN,case/NN,ru/JJ,atom/NN,regard/VB,stereogenic/JJ,centre/NN,complex/JJ,point/NN,chirality/NN,enantiomer/NN,complex/NN,ru/NN,bipyridine/NN,designate/VB,left/VB,handed/JJ,twist/NN,propeller/NN,ligand/NN,right/NN,handed/JJ,twist/NN,hexol/NN,chiral/JJ,cobalt/NN,compound/NN,definition/NN,racemic/JJ,chiral/JJ,substance/NN,scalemic/JJ,chiral/JJ,substance/NN,enantiopure/NN,homochiral/JJ,possible/JJ,enantiomer/NN,present/VB,chiral/JJ,substance/NN,enantioenrich/VB,heterochiral/JJ,excess/NN,enantiomer/NN,present/JJ,exclusion/NN,enantiomeric/NN,excess/NN,ee/NN,measure/NN,enantiomer/NN,present/JJ,compare/VB,example/NN,sample/NN,ee/NN,remaining/NN,racemic/JJ,total/JJ,enantiopure/JJ,preparation/NN,strategy/NN,exist/VB,preparation/NN,enantiopure/NN,compound/NN,method/NN,separation/NN,racemic/JJ,mixture/NN,isomer/NN,louis/NN,pasteur/NN,pioneer/VB,work/NN,able/JJ,isolate/VB,isomer/NN,tartaric/JJ,acid/NN,crystallize/VB,solution/NN,crystal/NN,differ/VB,symmetry/NN,common/JJ,recently/RB,discovered/JJ,method/NN,enantiomer/JJ,self/NN,advanced/JJ,technique/NN,involve/VB,separation/NN,primarily/RB,racemic/JJ,fraction/NN,nearly/RB,enantiopure/NN,fraction/NN,column/NN,chromatography/NN,symmetric/JJ,environment/NN,biological/JJ,environment/NN,enantiomer/NN,react/VB,different/JJ,speed/NN,substance/NN,basis/NN,chiral/JJ,synthesis/NN,preserve/VB,molecule/NN,desire/VB,chirality/NN,react/VB,catalyze/VB,chiral/JJ,molecule/NN,capable/JJ,maintain/VB,product/NN,chirality/NN,desired/JJ,conformation/NN,certain/JJ,chiral/JJ,molecule/NN,help/VB,configuration/NN,method/NN,exist/VB,organic/JJ,chemist/NN,synthesize/VB,maybe/RB,desire/VB,enantiomer/NN,reaction/NN,enantiopure/NN,medication/NN,advance/NN,industrial/JJ,chemical/NN,process/NN,allow/VB,pharmaceutical/JJ,manufacturer/NN,drug/NN,originally/RB,market/VB,racemic/JJ,form/NN,divide/VB,individual/NN,enantiomer/NN,unique/JJ,property/NN,drug/NN,zopiclone/NN,enantiomer/NN,eszopiclone/NN,active/JJ,fda/NN,allow/VB,generic/JJ,drug/NN,patent/VB,market/VB,case/NN,ibuprofen/NN,enantiomer/NN,produce/VB,effect/NN,steroid/JJ,receptor/NN,site/NN,stereoisomer/JJ,specificity/NN,example/NN,racemic/JJ,mixture/NN,enantiomer/NN,market/VB,include/VB,ofloxacin/JJ,floxin/NN,levofloxacin/NN,levaquin/NN,bupivacaine/NN,marcaine/NN,ropivacaine/NN,naropin/NN,methylphenidate/NN,ritalin/NN,focalin/NN,cetirizine/NN,zyrtec/NN,levocetirizine/NN,xyzal/NN,albuterol/NN,ventolin/NN,levalbuterol/NN,xopenex/JJ,omeprazole/NN,prilosec/NN,esomeprazole/NN,nexium/NN,citalopram/NN,celexa/NN,cipramil/NN,escitalopram/NN,lexapro/NN,cipralex/NN,zopiclone/NN,imovane/NN,eszopiclone/NN,lunesta/NN,modafinil/NN,provigil/NN,armodafinil/NN,nuvigil/JJ,sulfur/NN,chiral/JJ,center/NN,modafinil/NN,instead/RB,carbon/NN,chiral/JJ,drug/NN,high/JJ,enantiomeric/NN,purity/NN,potential/JJ,effect/NN,enantiomer/NN,enantiomer/NN,merely/RB,inactive/JJ,consider/VB,racemic/JJ,sample/NN,thalidomide/NN,enantiomer/NN,think/VB,effective/JJ,morning/NN,sickness/NN,know/VB,teratogenic/JJ,unfortunately/RB,case/NN,administer/VB,enantiomer/NN,pregnant/JJ,patient/NN,dangerous/JJ,enantiomer/NN,readily/RB,interconvert/VB,vivo/NN,person/NN,enantiomer/NN,isomer/NN,eventually/RB,present/JJ,patient/NN,serum/NN,chemical/JJ,process/NN,mitigate/VB,toxicity/NN,thalidomide/NN,enantiomer/NN,optical/JJ,activity/NN
12

Organic Chemistry/Dienes
organic/JJ,chemistry/NN,diene/NN,alkene/JJ,chemistry/NN,demonstrate/VB,allylic/JJ,carbon/NN,maintain/VB,cation/NN,charge/NN,double/JJ,bond/NN,localize/VB,support/VB,charge/NN,double/JJ,bond/NN,separate/VB,single/JJ,bond/NN,compound/NN,alternate/VB,double/JJ,bond/NN,single/JJ,bond/NN,addition/NN,concept/NN,chapter/NN,explore/VB,conjugate/VB,mean/VB,term/NN,stability/NN,reaction/NN,diene/NN,simply/RB,hydrocarbon/NN,contain/VB,double/JJ,bond/NN,diene/NN,intermediate/JJ,alkene/NN,polyene/NN,diene/NN,divide/VB,class/NN,unconjugated/JJ,diene/NN,double/JJ,bond/NN,separate/VB,single/JJ,bond/NN,know/VB,isolate/VB,diene/NN,conjugate/VB,diene/NN,conjugate/VB,double/JJ,bond/NN,separate/VB,single/JJ,bond/NN,cumulate/VB,diene/NN,cumulene/NN,double/JJ,bond/NN,share/VB,common/JJ,atom/NN,group/NN,compound/NN,allenes/JJ,kind/NN,diene/NN,conjugation/NN,diene/NN,property/NN,reaction/NN
13

Organic Chemistry/External links
organic/JJ,chemistry/NN,link/VB,online/JJ,organic/JJ,textbook/NN,resource/NN,iupac/NN,gold/NN,book/NN,definition/NN,online/JJ,textbook/NN,mit/VB,opencourseware/VB,organic/JJ,chemistry/NN,unfortunately/RB,information/NN,pdf/JJ,document/NN,instead/RB,html/NN,combinatorial/NN,chemistry/NN,basic/JJ,introduction/NN,field/NN,combinatorial/NN,chemistry/NN,mit/NN,opencourseware/VB,organic/JJ,chemistry/NN,ii/NN,pdf/NN,dilemma/NN,virtual/JJ,text/NN,real/JJ,nice/JJ,william/NN,reusch/NN,michigan/NN,state/NN,university/NN,crystal/NN,clear/JJ,chemistry/NN,good/JJ,resource/NN,study/VB,obtain/VB,answer/NN,conceptual/JJ,question/NN,aren/VB,answer/VB,chemhelper/JJ,com/NN,student/NN,arthur/JJ,winter/NN,frostburg/JJ,state/NN,university/NN,learnchem/VB,net/JJ,helpful/JJ,chemistry/NN,tutorial/NN,online/JJ,version/NN,lead/VB,text/NN,site/NN,extrapolating/NN,francis/NN,carey/NN,lead/VB,textbook/NN,general/JJ,chemistry/NN,reference/NN,visionlearn/VB,com/NN,fund/VB,national/JJ,science/NN,foundation/NN,lab/NN,technique/NN,compository/JJ,organic/JJ,chemistry/NN,portal/NN,organic/JJ,chemistry/NN,resource/NN,worldwide/JJ,length/NN,peer/VB,review/VB,free/JJ,organic/JJ,chemistry/NN,textbook/NN,download/VB,pdf/JJ,format/NN,academy/NN,colorful/JJ,clear/NN,engaging/JJ,organic/JJ,chemistry/NN,video/NN,playlist/NN,organic/JJ,chemistry/NN,practice/NN,problem/NN,collection/NN,organic/JJ,chemistry/NN,practice/NN,problem/NN,detailed/JJ,video/NN,solution/NN,google/NN,search/NN,result/NN
17

Organic Chemistry/Foundational concepts of organic chemistry/History of organic chemistry
atomic/JJ,structure/NN,brief/JJ,history/NN,gevela/NN,jacob/NN,berzelius/NN,physician/NN,trade/NN,coin/VB,term/NN,organic/JJ,chemistry/NN,study/NN,compound/NN,derive/VB,biological/JJ,source/NN,early/RB,century/NN,naturalist/NN,scientist/NN,observed/JJ,critical/JJ,difference/NN,compound/NN,derive/VB,living/JJ,thing/NN,chemist/NN,period/NN,note/VB,essential/JJ,inexplicable/JJ,difference/NN,property/NN,different/JJ,type/NN,compound/NN,vital/JJ,force/NN,theory/NN,vitalism/NN,vital/JJ,means/JJ,life/NN,force/NN,propose/VB,widely/RB,accept/VB,way/NN,explain/VB,difference/NN,vital/JJ,force/NN,exist/VB,organic/JJ,material/NN,exist/VB,inorganic/JJ,material/NN,synthesis/NN,urea/NN,urea/NN,friedrich/NN,wöhler/VB,widely/RB,regard/VB,pioneer/NN,organic/JJ,chemistry/NN,result/NN,synthesizing/NN,biological/JJ,compound/NN,urea/NN,component/NN,urine/NN,animal/NN,utilize/VB,wöhler/JJ,synthesis/NN,wöhler/VB,mixed/JJ,silver/NN,lead/VB,cyanate/NN,ammonium/NN,nitrate/NN,suppose/VB,yield/VB,ammonium/NN,cyanate/NN,result/NN,exchange/NN,reaction/NN,accord/VB,berzeliu/VB,dualism/NN,theory/NN,wöhler/VB,discover/VB,end/JJ,product/NN,reaction/NN,ammonium/NN,cyanate/NN,nh/NN,ocn/VB,inorganic/JJ,salt/NN,urea/NN,nh/RB,biological/JJ,compound/NN,furthermore/RB,heating/JJ,ammonium/NN,cyanate/NN,turn/VB,urea/NN,face/VB,result/NN,berzelius/NN,concede/VB,nh/RB,nh/RB,ocn/JJ,isomer/NN,discovery/NN,year/NN,widely/RB,believe/VB,chemist/NN,organic/JJ,substance/NN,form/VB,influence/NN,vital/JJ,force/NN,body/NN,animal/NN,plant/NN,wöhler/VB,synthesis/NN,dramatically/RB,prove/VB,view/NN,false/JJ,urea/NN,synthesis/NN,critical/JJ,discovery/NN,biochemist/NN,compound/NN,know/VB,produce/VB,nature/NN,biological/JJ,organism/NN,produce/VB,laboratory/NN,controlled/JJ,condition/NN,inanimate/JJ,matter/NN,synthesis/NN,organic/JJ,matter/NN,disprove/VB,common/JJ,theory/NN,vitalism/NN,vitali/NN,transcendent/JJ,life/NN,force/NN,need/VB,produce/VB,organic/JJ,compound/NN,organic/JJ,vs/NN,inorganic/JJ,chemistry/NN,originally/RB,define/VB,chemistry/NN,biological/JJ,molecule/NN,organic/JJ,chemistry/NN,redefine/VB,refer/VB,specifically/RB,carbon/NN,compound/NN,biological/JJ,origin/NN,carbon/NN,molecule/NN,consider/VB,organic/JJ,carbon/NN,dioxide/NN,know/VB,common/JJ,inorganic/JJ,carbon/NN,compound/NN,molecule/NN,exception/NN,rule/NN,organic/JJ,chemistry/NN,focus/VB,carbon/NN,following/JJ,movement/NN,electron/NN,carbon/NN,chain/NN,ring/NN,electron/NN,share/VB,carbon/NN,atom/NN,heteroatom/VB,organic/JJ,chemistry/NN,primarily/RB,concern/VB,property/NN,covalent/JJ,bond/NN,metallic/JJ,element/NN,ion/NN,metal/NN,play/VB,critical/JJ,role/NN,reaction/NN,application/NN,organic/JJ,chemistry/NN,myriad/JJ,include/VB,sort/NN,plastic/NN,dye/NN,flavoring/NN,scent/NN,detergent/NN,explosive/NN,fuel/NN,product/NN,read/VB,ingredient/NN,list/NN,kind/NN,food/NN,eat/VB,shampoo/NN,bottle/NN,handiwork/NN,organic/JJ,chemist/NN,list/VB,major/JJ,advance/NN,field/NN,organic/JJ,chemistry/NN,course/NN,chemistry/NN,text/NN,antoine/NN,laurent/NN,lavoisier/RB,french/JJ,chemist/NN,father/NN,modern/JJ,chemistry/NN,place/NN,pantheon/NN,great/JJ,chemistry/NN,figure/VB,general/JJ,chemistry/NN,textbook/NN,contain/VB,information/NN,specific/JJ,work/NN,discovery/NN,lavoisier/JJ,repeat/VB,discovery/NN,relate/VB,directly/RB,organic/JJ,chemistry/NN,particular/JJ,rico/NN,johnny/RB,discuss/VB,work/NN,foundational/JJ,specific/JJ,field/NN,organic/JJ,chemistry/NN,scientist/NN,fame/VB,independently/RB,propose/VB,element/NN,structural/JJ,theory/NN,chemist/NN,august/JJ,kekulé/NN,archibald/NN,quelantang/NN,rolando/VB,mangalindan/NN,kekulé/NN,german/NN,architect/NN,training/NN,propose/VB,isomerism/NN,carbon/NN,proclivity/NN,form/VB,bond/NN,ability/NN,bond/NN,atom/NN,ideal/VB,form/VB,long/JJ,chain/NN,atom/NN,single/JJ,molecule/NN,possible/JJ,number/NN,atom/NN,connect/VB,enormous/JJ,variety/NN,way/NN,couper/VB,scot/NN,butlerov/VB,russian/JJ,come/VB,conclusion/NN,time/NN,short/JJ,time/NN,nineteenth/JJ,century/NN,twentieth/JJ,experimental/JJ,result/NN,bring/VB,light/JJ,new/JJ,knowledge/NN,atom/NN,molecule/NN,molecular/JJ,bond/VB,gilbert/JJ,lewis/NN,berkeley/NN,covalent/JJ,bond/VB,largely/RB,know/VB,today/NN,electron/NN,sharing/NN,nobel/NN,laureate/NN,linus/NN,paul/VB,developed/JJ,lewis/NN,concept/NN,propose/VB,resonance/NN,california/NN,institute/NN,technology/NN,time/NN,sir/NN,robert/NN,robinson/NN,oxford/JJ,university/NN,focuse/VB,primarily/RB,electron/NN,atom/NN,engine/NN,molecular/JJ,change/NN,sir/NN,christopher/NN,ingold/NN,university/NN,college/NN,london/NN,organized/JJ,know/VB,organic/JJ,chemical/NN,reaction/NN,arrange/VB,scheme/NN,know/VB,mechanism/NN,order/NN,better/RB,understand/VB,sequence/NN,change/NN,synthesis/NN,reaction/NN,field/NN,organic/JJ,chemistry/NN,probably/RB,active/JJ,important/JJ,field/NN,chemistry/NN,moment/NN,extreme/JJ,applicability/NN,biochemistry/NN,especially/RB,pharmaceutical/JJ,industry/NN,petrochemistry/NN,especially/RB,energy/NN,industry/NN,organic/JJ,chemistry/NN,relatively/RB,recent/JJ,history/NN,enormously/RB,important/JJ,future/NN,affect/VB,life/NN,world/NN,year/NN,come/VB,alkane/NN
21

Wikibooks:Files to be harvested
list/NN,file/NN,upload/VB,serve/VB,source/NN,text/NN,image/NN,textbook/NN,project/NN,material/NN,freely/RB,project/NN,sure/JJ,use/VB,resource/NN,wise/JJ,legal/JJ,way/NN,wikibook/VB,medium/NN,organic/JJ,chemistry/NN,organic/JJ,chemistry/NN,basic/NN,german/NN,image/NN,useful/JJ,create/VB,upload/VB,magnus/NN,manske/NN,biochemistry/NN,biochemistry/NN,basic/NN,german/NN,image/NN,useful/JJ,create/VB,upload/VB,magnus/NN,manske/VB,online/JJ,reference/NN,list/NN,mathematics/NN,text/NN,include/VB,open/JJ,content/NN,book/NN,free/JJ,theassayer/NN,org/VB,public/JJ,domain/NN,textbook/NN,university/NN,pennsylvania/NN,lot/NN,old/JJ,dozen/NN,online/JJ,textbook/NN,investigate/VB,license/NN,wikipedia/NN,lot/NN,useful/JJ,gpl/NN,ed/NN,information/NN,need/VB,assimilate/VB,organize/VB,unified/JJ,project/NN,gutenberg/NN,countless/JJ,text/NN,link/VB,permission/NN,time/NN,use/VB,outside/JJ,material/NN,cc/NN,sa/NN,license/VB,public/JJ,domain/NN,experience/VB,wikipedia/NN,author/NN,place/VB,work/NN,free/JJ,license/NN,tend/NN,willing/JJ,grant/VB,cc/NN,sa/NN,license/NN,ask/VB,nicely/RB,boilerplate/NN,request/NN,permission/NN
32

Cookbook:Policy/Recipe template
notoc/NN,template/NN,page/NN,add/VB,recipe/NN,recommended/JJ,template/NN,recipe/NN,submit/VB,cookbook/NN,note/NN,guideline/NN,feel/VB,free/JJ,add/VB,section/NN,omit/VB,recipe/NN,need/VB,useful/JJ,dot/NN,represent/VB,relative/JJ,difficulty/NN,recipe/NN,description/NN,mind/NN,assign/VB,difficulty/NN,boil/VB,water/NN,right/NN,boil/VB,water/NN,right/RB,fairly/RB,easy/RB,fairly/RB,easy/JJ,medium/NN,difficulty/NN,medium/NN,difficulty/NN,fairly/RB,hard/RB,fairly/RB,hard/RB,iron/NN,chef/NN,iron/NN,chef/NN,image/NN,page/NN,useful/JJ,click/VB,bring/VB,list/NN,recipe/NN,particular/JJ,difficulty/NN,note/NN,borrow/VB,image/NN,german/NN,cookbook/NN,kochbuch/NN,wikibook/VB,org/JJ,domain/NN,german/NN,language/NN,recipe/NN,float/VB,list/NN,sample/NN,recipe/NN,template/NN,beef/NN,barley/NN,stew/NN,chocolate/NN,mousse/NN,tarbe/VB,salad/NN,template/NN,recipe/NN,submission/NN,cuisine/NN,type/NN,course/NN,short/JJ,description/NN,recipe/NN,sentence/NN,paragraph/NN,acceptable/JJ,dish/NN,normally/RB,prepared/JJ,story/NN,recipe/NN,creation/NN,anecdote/NN,perfectly/RB,acceptable/JJ,photo/NN,completed/JJ,dish/NN,helpful/JJ,lead/NN,section/NN,attach/VB,table/NN,ingredient/NN,cup/NN,ml/NN,item/NN,tablespoon/NN,ml/NN,item/NN,template/NN,page/NN,new/JJ,page/NN,new/JJ,ingredient/NN,list/VB,order/NN,procedure/NN,ingredient/NN,link/VB,pipe/NN,trick/NN,produce/VB,carrot/NN,optional/JJ,ingredient/NN,substitution/NN,list/NN,readable/JJ,place/NN,note/NN,tip/NN,variation/NN,section/NN,instead/RB,specific/JJ,different/JJ,cooking/JJ,procedure/NN,place/VB,second/JJ,list/NN,simply/RB,mark/VB,optional/JJ,consider/NN,separate/JJ,list/NN,shell/NN,meat/NN,sauce/NN,quantity/NN,list/VB,imperial/JJ,metric/JJ,recipe/NN,create/VB,equivalent/NN,value/NN,list/VB,immediately/RB,let/VB,user/NN,know/VB,unit/NN,original/JJ,estimate/VB,conversion/NN,provide/VB,volume/NN,measurement/NN,country/NN,kitchen/NN,simply/RB,equip/VB,measure/VB,mass/NN,weight/NN,yes/RB,lack/VB,balance/NN,scale/NN,specify/VB,size/NN,normal/JJ,chicken/NN,egg/NN,large/JJ,usa/NN,similar/JJ,size/NN,size/NN,eu/NN,country/NN,surely/RB,idea/NN,procedure/NN,step/VB,step/NN,template/NN,page/NN,new/JJ,page/NN,new/JJ,photo/NN,procedure/NN,complete/VB,thumb/NN,format/NN,caption/NN,identify/VB,step/NN,perform/VB,include/VB,pic/NN,note/VB,tip/NN,variation/NN,note/VB,tip/NN,variation/NN,area/NN,additional/JJ,information/NN,fit/NN,area/NN,recipe/NN,module/NN,warning/NN,warn/VB,warning/NN,external/JJ,link/NN,wikipedia/NN,link/NN,type/NN,talk/NN,page/NN,relevant/JJ,link/NN,type/NN,talk/NN,page/NN,talk/NN,page/NN,talk/NN,page/NN,cookbook/NN,related/JJ,template/NN,cookbook/NN,policy/NN,module/NN,category/NN,interlanguage/JJ,link/NN,place/VB,category/NN,scheme/NN,recipe/NN,category/NN,recipe/NN,template/NN,page/NN,add/VB,recipe/NN,mk/JJ,готвач/NN,шаблон/NN,за/NN,полиса/NN,рецепт/NN
43

Organic Chemistry/Foundational concepts of organic chemistry/Atomic structure
image/NN,simple/JJ,atom/NN,lithium/NN,png/VB,simple/JJ,model/NN,lithium/NN,atom/NN,scale/VB,atomic/JJ,structure/NN,atom/NN,nucleus/NN,electron/NN,orbit/NN,nucleus/NN,nucleus/NN,consist/VB,proton/NN,neutron/NN,atom/NN,natural/JJ,uncharged/JJ,state/NN,number/NN,electron/NN,proton/NN,nucleus/NN,nucleus/NN,proton/NN,positively/RB,charge/VB,neutron/NN,charge/NN,neutron/NN,proton/NN,mass/NN,account/NN,mass/NN,atom/NN,electron/NN,electron/NN,negatively/RB,charged/JJ,particle/NN,mass/NN,electron/NN,time/NN,smaller/JJ,proton/NN,neutron/NN,amu/JJ,electron/NN,circle/NN,fast/RB,determine/VB,electron/NN,point/NN,time/NN,image/NN,depict/VB,old/JJ,bohr/NN,model/NN,atom/NN,electron/NN,inhabit/VB,discrete/JJ,orbital/NN,nucleus/NN,planet/NN,orbit/NN,sun/NN,model/NN,outdated/JJ,current/JJ,model/NN,atomic/JJ,structure/NN,hold/VB,electron/NN,occupy/VB,fuzzy/JJ,cloud/NN,nucleus/NN,specific/JJ,shape/VB,spherical/JJ,dumbbell/NN,shape/VB,complex/JJ,shape/NN,shell/NN,orbital/VB,electron/NN,shell/NN,electron/NN,orbit/NN,atom/NN,cloud/NN,distinct/JJ,shape/NN,size/NN,electron/NN,cloud/NN,layer/VB,unit/NN,shell/NN,electron/NN,occupy/VB,simplest/JJ,orbital/NN,innermost/JJ,shell/NN,lowest/JJ,energy/NN,state/NN,electron/NN,complex/JJ,orbital/NN,outermost/JJ,shell/NN,highest/JJ,energy/NN,state/NN,higher/JJ,energy/NN,state/NN,energy/NN,electron/NN,rock/NN,hill/NN,potential/JJ,energy/NN,rock/NN,valley/NN,main/JJ,reason/NN,electron/NN,exist/VB,higher/JJ,energy/NN,orbital/NN,electron/NN,exist/VB,orbital/JJ,electron/NN,orbital/NN,lowest/JJ,energy/NN,orbital/NN,available/JJ,electron/NN,push/VB,higher/JJ,energy/NN,orbital/JJ,example/NN,photon/NN,typically/RB,stable/JJ,state/NN,electron/NN,descend/VB,lower/VB,energy/NN,state/NN,emit/VB,photon/NN,spontaneously/RB,concept/NN,important/JJ,understanding/NN,later/JJ,concept/NN,optical/JJ,activity/NN,chiral/JJ,compound/NN,interesting/JJ,phenomena/NN,realm/NN,organic/JJ,chemistry/NN,example/NN,laser/NN,work/VB,electron/NN,orbital/NN,different/JJ,shell/NN,subdivide/VB,orbital/NN,different/JJ,energy/NN,level/NN,energy/NN,difference/NN,orbital/NN,energy/NN,difference/NN,shell/NN,longer/JJ,wavelength/NN,energy/NN,orbital/JJ,longest/JJ,wavelength/NN,allow/VB,electron/NN,orbit/VB,nucleus/NN,orbital/JJ,observed/JJ,lowest/JJ,energy/NN,orbital/JJ,characteristic/JJ,shape/NN,electron/NN,exist/VB,orbital/NN,letter/NN,alphabet/NN,order/NN,increase/VB,energy/NN,orbital/NN,orbital/NN,progress/VB,shell/NN,represent/VB,principal/JJ,quantum/NN,number/NN,type/NN,orbital/NN,possible/JJ,shell/NN,designate/VB,number/NN,orbital/JJ,refer/VB,orbital/JJ,second/JJ,shell/NN,orbital/JJ,orbital/JJ,orbital/JJ,lowest/JJ,energy/NN,spherical/JJ,shape/NN,electron/NN,orbital/JJ,fundamental/JJ,frequency/NN,orbital/JJ,hold/VB,maximum/NN,electron/NN,image/NN,orbital/JJ,png/NN,orbital/JJ,lowest/JJ,energy/NN,orbital/JJ,orbital/JJ,shape/NN,like/JJ,dumbbell/NN,orbital/NN,oriented/JJ,dimensional/JJ,coordinate/NN,orbital/NN,hold/VB,maximum/NN,electron/NN,image/NN,orbital/JJ,png/NN,different/JJ,orbital/NN,refer/VB,px/NN,py/NN,pz/VB,orbital/NN,important/JJ,understand/VB,organic/JJ,chemistry/NN,orbital/NN,occupy/VB,type/NN,atom/NN,common/JJ,organic/JJ,compound/NN,orbital/NN,orbital/VB,orbital/NN,present/VB,transition/NN,metal/NN,sulphur/NN,phosphorus/NN,orbital/NN,compound/NN,involve/VB,atom/NN,orbital/NN,come/VB,play/NN,rarely/RB,organic/JJ,molecule/NN,present/VB,element/NN,lanthanide/NN,actinide/JJ,series/NN,lanthanide/NN,actinide/NN,irrelevant/JJ,organic/JJ,chemistry/NN,electron/NN,shell/NN,wp/JJ,electron/NN,configuration/NN,atom/NN,ion/NN,receive/VB,electron/NN,orbital/NN,orbital/NN,shell/NN,particular/JJ,manner/NN,principle/NN,govern/NN,process/NN,pauli/JJ,exclusion/NN,principle/NN,aufbau/NN,build/VB,principle/NN,hund/NN,rule/NN,pauli/NN,exclusion/NN,principle/NN,wp/NN,pauli/NN,exclusion/NN,principle/NN,electron/NN,atom/NN,quantum/NN,number/NN,translate/VB,term/NN,picture/NN,orbital/NN,orbital/JJ,hold/VB,electron/NN,spin/VB,spin/NN,hund/NN,rule/NN,state/NN,filled/JJ,half/NN,shell/NN,tend/VB,additional/JJ,stability/NN,instance/NN,example/NN,orbital/NN,orbital/NN,wp/NN,hund/NN,rule/NN,rule/NN,applicable/JJ,element/NN,electron/NN,important/JJ,organic/JJ,chemistry/NN,important/JJ,organometallic/JJ,chemistry/NN,octet/NN,rule/NN,octet/JJ,rule/NN,state/NN,atom/NN,tend/VB,prefer/VB,electron/NN,valence/NN,shell/VB,tend/VB,combine/VB,way/NN,atom/NN,electron/NN,valence/NN,shell/VB,similar/JJ,electronic/JJ,configuration/NN,noble/JJ,gas/NN,simple/JJ,term/NN,molecule/NN,stable/JJ,outer/JJ,shell/NN,constituent/NN,atom/NN,electron/NN,outer/JJ,shell/NN,main/JJ,exception/NN,rule/NN,helium/NN,lowest/JJ,energy/NN,electron/NN,valence/NN,shell/VB,notable/JJ,exception/NN,aluminum/NN,boron/NN,function/VB,valence/NN,electron/NN,atom/NN,group/NN,periodic/JJ,table/NN,electron/NN,sulfur/NN,additionally/RB,noble/JJ,gass/NN,form/VB,compound/NN,expand/VB,valence/NN,shell/VB,hybridization/NN,wp/JJ,orbital/JJ,hybridization/NN,hybridization/NN,refer/VB,combine/VB,orbital/NN,covalently/RB,bond/VB,atom/NN,depend/VB,free/JJ,electron/NN,atom/NN,bond/NN,form/VB,electron/NN,orbital/NN,combine/VB,certain/JJ,manner/NN,form/VB,bond/NN,easy/JJ,determine/VB,hybridization/NN,atom/NN,lewis/JJ,structure/NN,count/VB,number/NN,pair/NN,free/JJ,electron/NN,number/NN,sigma/NN,bond/NN,single/JJ,bond/NN,count/VB,double/JJ,bond/NN,affect/VB,hybridization/NN,atom/NN,total/NN,determine/VB,hybridization/NN,pattern/NN,follow/VB,sigma/NN,bond/NN,electron/NN,pair/NN,hybridization/NN,sp/NN,sp/NN,sp/NN,pattern/NN,electron/NN,orbital/NN,serve/VB,memory/NN,guide/NN,alkane/NN
47

Organic Chemistry/Foundational concepts of organic chemistry/Bonding
ionic/JJ,bond/VB,sodium/NN,chloride/NN,crystal/NN,structure/NN,atom/NN,nearest/NN,neighbor/NN,octahedral/JJ,geometry/NN,arrangement/NN,know/VB,cubic/JJ,close/VB,packed/JJ,ccp/NN,light/NN,blue/JJ,dark/JJ,green/NN,cl/VB,ionic/JJ,bond/VB,positively/RB,negatively/RB,charged/JJ,ion/NN,stick/NN,electrostatic/JJ,force/NN,bond/NN,slightly/RB,weaker/JJ,covalent/JJ,bond/NN,stronger/JJ,van/NN,der/NN,waal/VB,bond/VB,hydrogen/NN,bond/VB,ionic/JJ,bond/NN,negative/JJ,ion/NN,stronger/JJ,positive/JJ,ion/NN,ion/NN,share/NN,electron/NN,electronegative/JJ,ion/NN,assume/VB,ownership/NN,electron/NN,sodium/NN,chloride/NN,form/NN,crystal/NN,cubic/JJ,symmetry/NN,larger/JJ,chloride/NN,ion/NN,arrange/VB,cubic/JJ,close/NN,pack/VB,smaller/JJ,sodium/NN,ion/NN,octahedral/JJ,gap/NN,ion/NN,surround/VB,kind/NN,basic/JJ,structure/NN,mineral/NN,know/VB,halite/JJ,structure/NN,common/JJ,example/NN,ionically/RB,bond/VB,substance/NN,nacl/RB,table/NN,salt/NN,sodium/NN,atom/NN,electron/NN,electronegative/JJ,chlorine/NN,cl/JJ,atom/NN,atom/NN,ion/NN,cl/VB,electrostatic/JJ,bond/VB,force/NN,oppositely/VB,charged/JJ,ion/NN,extend/VB,local/JJ,area/NN,attract/VB,ion/NN,form/VB,giant/JJ,crystal/NN,structure/NN,reason/NN,ionically/RB,bond/VB,material/NN,solid/JJ,room/NN,temperature/NN,covalent/VB,bond/VB,covalent/JJ,bond/VB,close/JJ,heart/NN,organic/JJ,chemistry/NN,atom/NN,share/NN,electron/NN,bond/NN,goal/NN,atom/NN,octet/NN,formal/JJ,charge/NN,atomic/JJ,nuclei/NN,share/NN,electron/NN,space/NN,sharing/NN,allow/VB,atom/NN,reach/VB,lower/JJ,energy/NN,state/NN,stabilize/VB,molecule/NN,reaction/NN,chemistry/NN,molecule/NN,achieve/VB,lower/JJ,energy/NN,state/NN,covalent/JJ,bond/NN,frequently/RB,atom/NN,similar/JJ,molecule/NN,type/NN,atom/NN,atom/NN,necessarily/RB,identical/JJ,form/VB,ionic/JJ,bond/NN,form/VB,covalent/JJ,bond/NN,carbon/NN,especially/RB,good/JJ,covalent/JJ,bond/VB,intermediate/JJ,relative/JJ,atom/NN,mean/VB,electron/NN,needs/JJ,warrant/NN,covalently/VB,bond/VB,compound/NN,strong/JJ,internal/JJ,bond/NN,weak/JJ,attractive/JJ,force/NN,molecule/NN,weak/JJ,attractive/JJ,force/NN,melting/NN,boil/VB,point/NN,compound/NN,lower/JJ,compound/NN,ionic/JJ,bond/NN,compound/NN,likely/JJ,liquid/NN,gase/NN,room/NN,temperature/NN,ionically/RB,bond/VB,compound/NN,molecule/NN,form/VB,atom/NN,element/NN,difference/NN,bond/VB,atom/NN,electron/NN,covalent/JJ,bond/NN,share/VB,equally/RB,result/VB,completely/RB,polar/JJ,covalent/JJ,bond/NN,covalent/JJ,bond/NN,bond/VB,atom/NN,different/JJ,element/NN,difference/NN,atom/NN,atom/NN,electronegative/JJ,attract/VB,bond/VB,electron/NN,electronegative/JJ,atom/NN,difference/NN,charge/NN,atom/NN,electron/NN,cause/VB,covalent/JJ,bond/NN,polar/JJ,greater/JJ,difference/NN,result/NN,polar/JJ,bond/NN,depend/VB,difference/NN,polarity/NN,bond/NN,range/VB,polar/JJ,covalent/NN,ionic/JJ,vary/VB,degree/NN,polar/JJ,covalent/NN,overall/JJ,imbalance/NN,charge/NN,molecule/NN,dipole/JJ,moment/NN,molecule/NN,polar/JJ,completely/RB,symmetrical/JJ,covalently/NN,bond/VB,molecule/NN,overall/JJ,dipole/JJ,moment/NN,molecule/NN,molecule/NN,larger/JJ,dipole/JJ,moment/NN,polar/JJ,common/JJ,polar/JJ,molecule/NN,water/NN,bond/NN,polarity/NN,dipole/JJ,moment/NN,methane/NN,idea/NN,bond/NN,polarity/NN,dipole/JJ,moment/NN,play/NN,important/JJ,role/NN,organic/JJ,chemistry/NN,look/VB,image/NN,methane/NN,right/RB,single/JJ,important/JJ,aspect/NN,term/NN,bond/NN,polarity/NN,symmetric/JJ,molecule/NN,hydrogen/NN,bond/VB,precisely/RB,bond/NN,angle/NN,carbon/NN,hydrogen/NN,bond/NN,slightly/RB,polar/JJ,hydrogen/NN,carbon/NN,symmetry/NN,polarity/NN,cancel/VB,overall/JJ,methane/NN,polar/JJ,molecule/NN,distinction/NN,bond/NN,polarity/NN,molecular/JJ,polarity/NN,total/NN,polarity/NN,molecule/NN,measure/VB,dipole/JJ,moment/NN,actual/JJ,calculation/NN,dipole/JJ,moment/NN,isn/NN,necessary/JJ,understanding/NN,mean/VB,frequently/RB,guesstimate/NN,dipole/JJ,moment/NN,pretty/RB,easy/JJ,understand/VB,concept/NN,advanced/JJ,organic/JJ,chemistry/NN,exact/JJ,value/NN,little/JJ,value/NN,basically/RB,molecular/JJ,polarity/NN,essentially/RB,summation/NN,vector/NN,bond/NN,polarity/NN,molecule/NN,van/NN,der/NN,waal/VB,bond/VB,van/NN,waal/NN,bond/VB,collective/JJ,type/NN,interaction/NN,permanent/JJ,dipole/JJ,interaction/NN,electrostatic/JJ,attractive/JJ,force/NN,dipole/NN,responsible/JJ,fluromethane/NN,ch/JJ,high/JJ,boil/VB,point/NN,deg/JJ,compare/VB,nitrogen/NN,deg/JJ,permanent/JJ,dipole/JJ,induced/JJ,dipole/JJ,interaction/NN,permanent/JJ,dipole/JJ,molecule/NN,cause/VB,molecule/NN,electron/NN,cloud/NN,distort/VB,induced/JJ,dipole/JJ,weaker/JJ,permanent/JJ,dipole/JJ,dipole/JJ,interaction/NN,force/NN,occur/VB,permanent/JJ,dipole/JJ,molecule/NN,mixture/NN,permanent/JJ,dipole/JJ,dipole/JJ,free/JJ,molecule/NN,instantaneous/JJ,dipole/JJ,induced/JJ,dipole/JJ,specific/JJ,moment/NN,electron/NN,cloud/NN,necesarily/RB,instantaneous/JJ,dipole/JJ,induce/VB,dipole/JJ,molecule/NN,attract/VB,weakest/JJ,molecular/JJ,interaction/NN,dipole/JJ,cause/VB,atom/NN,molecule/NN,fragment/NN,higher/JJ,measure/NN,effective/JJ,nuclear/JJ,charge/NN,attraction/NN,nucleus/NN,electron/NN,attach/VB,mean/VB,pull/VB,electron/NN,closer/JJ,higher/JJ,share/NN,electron/NN,bond/NN,dipole/NN,cancel/VB,symmetry/NN,carbon/NN,dioxide/NN,linear/JJ,dipole/JJ,charge/NN,distribution/NN,asymmetric/JJ,cause/VB,quadripole/JJ,moment/NN,act/VB,similarly/RB,dipole/JJ,weaker/JJ,organometallic/JJ,compound/NN,bond/VB,organometallic/JJ,chemistry/NN,combine/VB,aspect/NN,inorganic/JJ,chemistry/NN,organic/JJ,chemistry/NN,organometallic/JJ,compound/NN,chemical/JJ,compound/NN,contain/VB,bond/NN,carbon/NN,metal/NN,metalloid/JJ,element/NN,organometallic/JJ,bond/NN,different/JJ,bond/NN,truly/RB,covalent/JJ,truly/RB,ionic/JJ,type/NN,metal/NN,individual/JJ,bond/NN,character/NN,cuprate/JJ,copper/NN,compound/NN,example/NN,behave/VB,differently/RB,grignard/NN,reagent/NN,magnesium/NN,beginning/JJ,organic/JJ,chemist/NN,concentrate/VB,use/VB,basic/JJ,compound/NN,mechanistically/RB,leave/VB,explanation/NN,exactly/RB,occur/VB,molecular/JJ,level/NN,later/JJ,depth/NN,study/NN,subject/JJ,basic/JJ,organometallic/JJ,interaction/NN,discuss/VB,fully/RB,later/JJ,chapter/NN,alkane/NN
53

Organic Chemistry/Foundational concepts of organic chemistry/Resonance
resonance/NN,resonance/NN,refer/VB,structure/NN,easily/RB,represent/VB,single/JJ,electron/NN,dot/NN,structure/NN,intermediate/NN,draw/VB,structure/NN,resonance/NN,easily/RB,misunderstand/VB,way/NN,certain/JJ,chemistry/NN,textbook/NN,attempt/VB,explain/VB,concept/NN,science/NN,analogy/NN,provide/VB,aid/NN,understanding/NN,analogy/NN,literally/RB,best/RB,use/VB,analogy/NN,introduce/VB,topic/NN,explain/VB,difference/NN,inevitable/JJ,complication/NN,complicated/JJ,subject/NN,case/NN,resonance/NN,entropic/JJ,principle/NN,apply/VB,individual/JJ,molecule/NN,impossible/JJ,individual/JJ,molecule/NN,resonance/NN,structure/NN,literally/RB,configuration/NN,actual/JJ,situation/NN,molecular/JJ,scale/NN,configuration/NN,molecule/NN,contribute/VB,percentage/NN,possible/JJ,configuration/NN,result/VB,blend/NN,possible/JJ,structure/NN,change/NN,molecular/JJ,shape/NN,occur/VB,rapidly/RB,tiny/JJ,scale/NN,actual/JJ,physical/JJ,location/NN,individual/JJ,electron/NN,precisely/RB,know/VB,heisenberg/VB,uncertainty/NN,principle/NN,result/NN,complexity/NN,simply/RB,molecule/NN,resonance/NN,structure/NN,treat/VB,mixture/NN,multiple/JJ,form/NN,greater/JJ,percentage/NN,probability/NN,stable/JJ,configuration/NN,nuclei/NN,atom/NN,represent/VB,resonance/NN,structure/NN,drawing/NN,electron/NN,portray/VB,instead/RB,true/JJ,situation/NN,certain/JJ,exactly/RB,individual/JJ,electron/NN,specific/JJ,moment/NN,electron/NN,location/NN,express/VB,probability/NN,dot/NN,structure/NN,actually/RB,showing/NN,electron/NN,certainly/RB,locate/VB,resonance/NN,structure/NN,indicate/VB,split/NN,probability/NN,chemist/NN,absolutely/RB,certain/JJ,electron/NN,locate/VB,carbon/NN,bond/NN,hydrogen/NN,methane/NN,certain/JJ,precisely/RB,electron/NN,locate/VB,carbon/NN,bond/NN,hydrogen/NN,ring/NN,structrue/JJ,benzene/NN,resonance/NN,expression/NN,uncertainty/NN,average/NN,probable/JJ,location/NN,resonance/NN,structure/NN,stabilize/VB,molecule/NN,allow/VB,electron/NN,lengthen/VB,wavelength/NN,lower/VB,energy/NN,reason/NN,benzene/NN,lower/JJ,heat/NN,formation/NN,organic/JJ,chemist/NN,predict/VB,accounting/NN,resonance/NN,aromatic/JJ,molecule/NN,similar/JJ,stability/NN,lead/VB,overall/JJ,entropic/NN,preference/NN,aromaticity/NN,subject/NN,cover/VB,fully/RB,later/JJ,chapter/NN,resonance/NN,stability/NN,play/VB,major/JJ,role/NN,organic/JJ,chemistry/NN,resonant/JJ,molecule/NN,lower/JJ,energy/NN,formation/NN,student/NN,organic/JJ,chemistry/NN,understand/VB,effect/NN,practice/NN,spotting/JJ,molecule/NN,stabilize/VB,resonant/JJ,form/NN,carbonate/NN,lewis/NN,structure/NN,carbonate/NN,resonance/NN,structure/NN,laboratory/NN,procedure/NN,measure/VB,bond/NN,length/NN,bond/NN,bond/NN,shorter/JJ,remember/VB,double/JJ,bond/NN,shorter/JJ,single/JJ,bond/NN,instead/RB,bond/NN,length/NN,length/NN,typical/JJ,double/NN,single/JJ,bond/NN,resonance/NN,structure/NN,scheme/NN,resonance/NN,structure/NN,benzene/NN,resonance/NN,structure/NN,diagrammatic/JJ,tool/NN,predominately/RB,organic/JJ,chemistry/NN,symbolize/VB,resonant/JJ,bond/NN,atom/NN,molecule/NN,electron/NN,density/NN,bond/NN,spread/VB,molecule/NN,know/VB,delocalization/NN,electron/NN,resonance/NN,contributor/NN,molecule/NN,chemical/NN,formula/NN,sigma/NN,framework/NN,pi/NN,electron/NN,distribute/VB,differently/RB,atom/NN,lewis/JJ,dot/NN,diagram/NN,represent/VB,true/JJ,electronic/JJ,structure/NN,molecule/NN,resonance/NN,structure/NN,employ/VB,approximate/JJ,true/JJ,electronic/JJ,structure/NN,resonance/NN,structure/NN,molecule/NN,connect/VB,double/NN,head/VB,arrow/NN,organic/JJ,chemist/NN,use/VB,resonance/NN,structure/NN,frequently/RB,inorganic/JJ,structure/NN,nitrate/NN,example/NN,key/JJ,characteristic/NN,key/JJ,element/NN,resonance/NN,resonance/NN,occur/VB,overlap/NN,orbital/NN,double/JJ,bond/NN,pi/NN,bond/NN,form/VB,overlap/NN,orbital/VB,electron/NN,pi/NN,orbital/NN,spread/VB,atom/NN,delocalize/VB,pair/VB,unshared/JJ,electron/NN,delocalize/VB,electron/NN,conjugate/VB,pi/NN,orbital/NN,overlap/JJ,orthogonal/JJ,orbital/NN,structure/NN,true/JJ,resonance/NN,structure/NN,mix/NN,molecule/NN,species/NN,resonance/NN,structure/NN,generally/RB,consider/VB,stable/JJ,delocalization/NN,electron/NN,lower/VB,orbital/JJ,energy/NN,impart/VB,stability/NN,resonance/NN,benzene/NN,rise/JJ,property/NN,aromaticity/NN,gain/NN,stability/NN,resonance/NN,energy/NN,resonance/NN,structure/NN,molecule/NN,sigma/NN,framework/NN,sigma/NN,bond/NN,form/VB,head/NN,overlap/NN,hybridized/JJ,orbital/NN,furthermore/RB,correct/JJ,lewis/NN,structure/NN,number/NN,electron/NN,consequent/JJ,charge/NN,number/NN,unpair/VB,electron/NN,resonance/NN,structure/NN,arbitrary/JJ,separation/NN,charge/NN,unimportant/JJ,fewer/JJ,covalent/NN,bond/NN,unimportant/JJ,resonance/NN,structure/NN,contribute/VB,minimally/RB,overall/JJ,bond/VB,description/NN,important/JJ,case/NN,carbonyl/NN,group/NN,hybrid/JJ,structure/NN,defined/JJ,superposition/NN,resonance/NN,structure/NN,benzene/NN,ring/NN,circle/NN,hexagon/NN,american/JJ,text/NN,alternate/VB,double/JJ,bond/NN,example/NN,misrepresent/VB,electronic/JJ,structure/NN,bond/NN,broken/JJ,bond/NN,order/NN,display/VB,double/JJ,bond/NN,solid/JJ,dashed/JJ,line/NN,resonance/NN,significantly/RB,resonance/NN,structure/NN,represent/VB,different/JJ,isolatable/JJ,structure/NN,compound/NN,case/NN,benzene/NN,example/NN,important/JJ,resonance/NN,structure/NN,think/VB,cyclohexa/NN,triene/VB,resonance/NN,form/NN,possible/JJ,higher/RB,energy/NN,triene/NN,structure/NN,charge/VB,separation/NN,effect/NN,important/JJ,contribute/VB,real/JJ,electronic/JJ,structure/NN,average/JJ,hybrid/NN,mean/VB,different/JJ,form/NN,benzene/NN,true/JJ,electronic/JJ,structure/NN,benzene/NN,average/NN,structure/NN,carbon/NN,carbon/NN,bond/NN,length/NN,identical/JJ,invalid/JJ,cyclic/NN,triene/NN,resonance/NN,confuse/VB,chemical/NN,equilibrium/NN,tautomerism/NN,equilibrium/NN,compound/NN,different/JJ,sigma/NN,bond/VB,pattern/NN,special/JJ,case/NN,resonance/NN,history/NN,concept/NN,resonance/NN,introduce/VB,linus/NN,pauling/NN,inspire/VB,quantum/NN,mechanical/JJ,treatment/NN,ion/NN,electron/NN,locate/VB,hydrogen/NN,nuclei/NN,alternative/JJ,term/NN,mesomerism/NN,popular/JJ,german/NN,french/JJ,publication/NN,meaning/NN,introduce/VB,christopher/NN,ingold/NN,catch/VB,english/NN,literature/NN,current/JJ,concept/NN,mesomeric/JJ,effect/NN,related/JJ,different/JJ,meaning/NN,double/JJ,head/VB,arrow/NN,introduce/VB,german/NN,chemist/NN,arndt/NN,responsible/JJ,arndt/NN,eistert/JJ,synthesis/NN,prefer/VB,german/NN,phrase/NN,intermediate/JJ,phase/NN,confusion/NN,physical/JJ,meaning/NN,word/NN,resonance/NN,element/NN,actually/RB,appear/VB,resonate/VB,suggest/VB,abandon/VB,term/NN,resonance/NN,favor/NN,delocalization/NN,resonance/NN,energy/NN,delocalization/JJ,energy/NN,resonance/NN,structure/NN,contribute/VB,structure/NN,double/JJ,headed/JJ,arrow/NN,replace/VB,comma/NN,example/NN,scheme/NN,example/NN,resonance/NN,ozone/NN,benzene/NN,allyl/NN,cation/NN,ozone/NN,molecule/NN,represent/VB,resonance/NN,structure/NN,scheme/NN,reality/NN,terminal/JJ,oxygen/NN,atom/NN,equivalent/JJ,hybrid/JJ,structure/NN,draw/VB,right/NN,charge/NN,oxygen/NN,atom/NN,partial/JJ,double/JJ,bond/NN,concept/NN,benzene/NN,hybrid/NN,conventional/JJ,structure/NN,middle/JJ,scheme/NN,major/JJ,breakthrough/NN,chemistry/NN,kekule/NN,form/NN,ring/NN,represent/VB,total/JJ,resonance/NN,kekule/NN,structure/NN,hybrid/JJ,structure/NN,right/RB,circle/NN,replace/VB,double/JJ,bond/NN,allyl/NN,cation/NN,scheme/NN,resonance/NN,form/NN,hybrid/JJ,structure/NN,positive/JJ,charge/NN,delocalize/VB,terminal/JJ,methylene/NN,group/NN,delocalization/JJ,reference/NN,resonance/NN,resonate/VB,kerber/NN,robert/JJ,chem/VB,educ/JJ,abstract/JJ,text/NN,originally/RB,http/NN,wikipedia/NN,org/NN,index/NN,php/NN,title/NN,resonance/NN,chemistry/NN,oldid/VB,alkane/NN
54

In [5]:

    

import nltk
from nltk.collocations import TrigramCollocationFinder
from nltk.metrics import BigramAssocMeasures, TrigramAssocMeasures

def best_ngrams(words, top_n=1000, min_freq=100):
    """
    Extract `top_n` most salient collocations (bigrams and trigrams),
    from a stream of words. Ignore collocations with frequency
    lower than `min_freq`.

    This fnc uses NLTK for the collocation detection itself -- not very scalable!

    Return the detected ngrams as compiled regular expressions, for their faster
    detection later on.

    """
    tcf = TrigramCollocationFinder.from_words(words)
    tcf.apply_freq_filter(min_freq)
    trigrams = [' '.join(w) for w in tcf.nbest(TrigramAssocMeasures.chi_sq, top_n)]
    logging.info("%i trigrams found: %s..." % (len(trigrams), trigrams[:20]))

    bcf = tcf.bigram_finder()
    bcf.apply_freq_filter(min_freq)
    bigrams = [' '.join(w) for w in bcf.nbest(BigramAssocMeasures.pmi, top_n)]
    logging.info("%i bigrams found: %s..." % (len(bigrams), bigrams[:20]))

    pat_gram2 = re.compile('(%s)' % '|'.join(bigrams), re.UNICODE)
    pat_gram3 = re.compile('(%s)' % '|'.join(trigrams), re.UNICODE)

    return pat_gram2, pat_gram3


    

In [65]:

    

class Wikibooks_Collocations(object):
    def __init__(self, fname, max_number_of_books=None, min_freq=20):
        self.fname = fname
        self.min_freq = min_freq
        logging.info("collecting ngrams from %s" % self.fname)
        # generator of books; one element = list of words
        i = 0
        words = []
        for title, tokens in self.parse_wikibooks():
            #print "%s\n%s\n%s" % (title, ','.join(tokens), pageid)
            #print
            words += tokens
            i += 1
            if max_number_of_books is not None and  i >= max_number_of_books:
                break
                
        #books = (self.split_words(text) for text in iter_20newsgroups(self.fname, log_every=1000))
        self.bigrams, self.trigrams = best_ngrams(words, min_freq=self.min_freq)

    def process_book(self, (title, text)):
        """
        Parse a wikipedia article, returning its content as
        `(title, list of tokens)`, all utf8.

        """
        text = gensim.corpora.wikicorpus.filter_wiki(text) # remove markup, get plain text
        # tokenize plain text, throwing away sentence structure, short words etc
        #tokens = gensim.utils.lemmatize(text, stopwords=STOPWORDS)
        tokens = gensim.utils.simple_preprocess(text)
        return title.encode('utf8'), [token for token in tokens if token not in STOPWORDS]

    def parse_wikibooks(self):
        """
        Yield articles from a bz2 Wikibooks dump `infile` as (title, tokens) 2-tuples.

        Only articles of sufficient length are returned (short articles & redirects
        etc are ignored).

        Uses multiple processes to speed up the parsing in parallel.

        """
        ignore_namespaces = 'Wikipedia Category File Portal Template MediaWiki User Help Book Draft'.split()
        # process the corpus in smaller chunks of docs, because multiprocessing.Pool
        # is dumb and would try to load the entire dump into RAM...
        for title, text, pageid in gensim.corpora.wikicorpus._extract_pages(smart_open(self.fname)):
            title, tokens = self.process_book((title, text))
            if len(tokens) < 50 or any(title.startswith(ns + ':') for ns in ignore_namespaces):
                continue  # ignore short articles and various meta-articles
            yield title.replace('\t', ' '), tokens
    
    def entity_replace(self, tokens):
        """    
        The resulting tokens can be longer phrases (collocations) too,
        e.g. `new_york`, `real_estate` etc.

        """
        text = u' '.join(tokens)
        text = re.sub(self.trigrams, lambda match: match.group(0).replace(u' ', u'_'), text)
        text = re.sub(self.bigrams, lambda match: match.group(0).replace(u' ', u'_'), text)
        return text.split()

    def __iter__(self):
        for title, tokens in self.parse_wikibooks():
            yield title, self.entity_replace(tokens)


    

In [75]:

    

%time wiki_colloc = Wikibooks_Collocations('data/enwikibooks-20150314-pages-articles.xml.bz2',\
                                           max_number_of_books=10000,\
                                           min_freq=100)
for title, tokens in itertools.islice(wiki_colloc, 3):
    print "%s\n%s\n" % (title, ' '.join(tokens))


    

    




INFO:root:collecting ngrams from data/enwikibooks-20150314-pages-articles.xml.bz2
INFO:root:65 trigrams found: [u'radiat oncol biol', u'oncol biol phys', u'bie deploy plugins', u'oo oo oo', u'potter deathly hallows', u'totalt drwxr xr', u'atlas shrugged settings', u'places atlas shrugged', u'drwxr xr root', u'int radiat oncol', u'atlas shrugged appear', u'local bie deploy', u'usr local bie', u'characters atlas shrugged', u'defence dark arts', u'requirements workbook requirements', u'field guide birds', u'notes tips variations', u'half blood prince', u'root drwxr xr']...
INFO:root:552 bigrams found: [u'invisibility cloak', u'rob horning', u'deathly hallows', u'atlas shrugged', u'prisoner azkaban', u'bile duct', u'cellular automata', u'biol phys', u'spinal cord', u'vice versa', u'radical prostatectomy', u'cleft palate', u'console writeline', u'deploy plugins', u'hospital wing', u'barset skip', u'chamber secrets', u'ff ff', u'autosomal dominant', u'dou\u0103 sute']...






    




Wall time: 1min 49s
Main Page
overview wikibooks questions help browse science social sciences subjects languages mathematics miscellaneous computing engineering humanities welcome wikibooks open content textbooks collection edit books pages style width padding px vertical align background color ddddff style width padding px vertical align background color ddddff style width padding px vertical align background color ddddff

Organic Chemistry/Cover
welcome world foremost open content organic_chemistry textbook web contents image ethane png free online text intended complete replacement printed book study organic_chemistry organic_chemistry primarily devoted unique properties carbon atom compounds compounds play critical role biology ecology earth sciences geology physics industry medicine course chemistry glance new material organic_chemistry brings table complicated daunting takes concentration perseverance millions students successfully passed course field chemistry based formulas reactions molecules different conditions typical general chemistry question ask student compute answer equation chapter memorized typical organic_chemistry question lines product form substance treated solution bombarded light key learning organic_chemistry understand cram night test good memorize mechanism michael addition superior accomplishment ability explain reaction place things easier build body new knowledge foundation solid prior knowledge students served knowledge brought subject subject general chemistry concepts particular importance organic chemists covalent bonding molecular orbit theory vsepr modeling understanding acid base chemistry vis vis pka values trends periodic table means comprehensive list knowledge gained order fully understand subject organic_chemistry idea things need_know succeed organic_chemistry test course organic_chemistry subjects varying useful close daily life try figure unknown mysteries daily life factious thinking habit generates superstitions help chemistry help kind superstition try ultimate truth convenience ancient past struggled things need context house food transportation burning question chemistry help daily life answer_questions know subject thoroughly let start

Organic Chemistry/Alkenes
alkenes aliphatic hydrocarbons containing carbon carbon double_bonds general formula cnh naming alkenes alkenes named alkanes ane suffix changed ene alkene contains double_bond double_bond terminal double_bond end molecule necessary place number butane ch_ch ch_ch butene ch_chch_ch double_bond terminal carbon center chain carbons numbered way double_bonded carbons lowest possible number_number precede ene suffix dash shown correct pent ene ch_ch chch_ch incorrect pent ene ch_ch ch_chch second incorrect flipping formula horizontally results lower number alkene double_bond alkene bonds numbered molecule terminal double_bonds numbers lowest highest separated comma iupac numerical prefixes indicate number double_bonds octa diene ch_ch chch_chch_ch ch deca diene ch_chch_ch ch_chch_ch ch_ch note numbering yields molecule double_bonds separated single bond double_bonds condition called conjugated represent enhanced stability conformation energetically favored reactants situations combinations ez notation earlier stereochemistry discussed cis trans notation cis means trans means opposite alkenes present unique problem cis trans notation breaks thing mind alkenes planar rotation bonds ll discuss later substituent double_bond stays cis ene trans ene example pretty straight forward left methyl groups cis ene right opposite sides trans ene situation cis trans notation works fact correct names methylpent ene methylpent ene example_use cis trans opposite alkene differing substituents use called ez nomenclature coming german words entgegen opposite zusammen entgegen opposite sides double_bond zusammen sides zame zides double_bond let begin methylpent ene begin dividing alkene left_right halves assign substituent high priority low priority substituent priority based atomic number substituents left hydrogen lowest priority atomic number carbon higher atomic number right carbon substituents bond carbon hydrogen gets high priority gets low priority high priorities sides zusammen mnemonic think zame zide let_look methylpent ene left substituents sides priorities zusammen version substituents reversed right high priority substituent low priority substituent high low priorities opposite left_right entgegen opposite takes little getting usually easier alkene write given little practice ll easy comparison cis trans ene ene image cis butene png_image trans butene png cis ene trans ene certain extent configuration regarded cis isomer trans isomers correspondence exact carbon atoms identically substituted general cis trans double_bonded carbon atom hydrogen atom ch_ch iupac gold book cis trans notation iupac gold book notation properties alkenes molecules carbons bonded hydrogens contain sp hybridized carbon atoms carbon carbon double_bond carbon atoms addition electron pair shared sigma bond share pair electrons pi bond general formula aliphatic alkene cnh diastereomerism restricted rotation characteristics pi bonds alkenes limited rotation double_bonds atoms order alkene structure rotate pi bond broken require kcal energy reason alkenes different chemical properties based bond atom located example ene exists diastereomers ene ene image cis butene png_image trans butene png cis ene trans ene relative stability observing reaction addition hydrogen butene butene butene products butane difference reactions reaction different energy kcal mol butene kcal mol butene kcal mol butene illustrates differences stabilities species butene isomers difference energy released reducing relative stability alkenes estimated based following concepts internal alkene double_bond terminal carbon stable terminal alkene double_bond terminal carbon internal alkenes stable terminal alkenes connected carbons chain terminal alkene located end chain double_bond connected carbon called primary primary carbons stable middle chain double_bond connected carbons called secondary stable quaternary general bulkier alkyl groups sp hybridized carbon alkene stable alkene trans double_bond stable cis double_bond reactions preparation methods creating alkenes methods wittig reaction ll briefly chapter instead cover later book know ways creating alkenes haloalkanes synthesis alkene alkyl halides converted alkenes elimination elements hydrogen halide involves removal halogen atom hydrogen atom carbon adjacent bearing halogen uses elimination mechanism ll discuss end chapter haloalkane hydrogen halide neighboring carbons hydrogen halogen neighboring carbon reaction place surprising reagent required elimination amounts molecule acid strong base example alcholic koh cases reaction yields single alkene cases yield mixture butyl chloride example eliminate hydrogen yields butene sec butyl chloride hand eliminate hydrogen yields butene butene alkenes formed butene chief product dehalogenation vicinal dibromides synthesis alkene debromination vicinal dihalides sodium iodide synthesis alkene debromination vicinal dihalides zinc dehalogenation vicinal dihalides halides neighboring carbons think vicinity method synthesizing alkenes reaction place sodium iodide solution acetone performed zinc dust solution heated ethanol acetic acid reaction performed magnesium ether mechanism different actually produces intermediate grignard reagent reacts causes elimination resulting alkene dehydration alcohols synthesis alkene dehydration alcohol alcohol converted alkene dehydration elimination molecule water dehydration requires presence acid application heat generally carried ways heating alcohol sulfuric phosphoric acid temperatures high passing alcohol vapor alumina al alumina serving lewis acid ease dehydration alcohols isomeric alkenes formed tendency isomer predominate sec butyl alcohol yield butene butene actually yields exclusively isomer formation butene butyl alcohol illustrates characteristic dehydration shared double_bond formed position remote carbon originally holding oh group characteristic accounted later chiefly greater certainty double_bond appear preferred dehydration method making alkenes reduction alkenes reduction alkene double_bond stage triple bond end chain yield cis alkene trans alkene isomer predominates depends choice reducing agent predominantly trans alkene obtained reduction alkenes sodium lithium liquid ammonia entirely cis alkene high obtained hydrogenation alkenes different catalysts specially prepared palladium called lindlar catalyst nickel boride called catalyst reactions highly stereoselective cis reduction alkynes attributed general way attachment hydrogens alkyne sitting catalyst surface presumably stereochemistry holds hydrogenation terminal alkenes yield cis trans alkenes wittig reaction synthesis alkene wittig reaction markovnikov rule continue discussing reactions need detour discuss subject important alkene reactions markovnikov rule simple rule stated russian vladmir markovnikov showing orientation addition hbr alkenes rule states unsymmetrical alkene reacts hydrogen halide alkyl halide hydrogen adds carbon alkene greater number hydrogen substituents halogen carbon alkene fewer number hydrogen substituents rule compared phrase rich richer poor poorer aka carbon hydrogens gets hydrogen hydrogens gets halogen means nucleophile electophile nucleophile pair bonded position stable carbocation partial positive_charge case transition state examples br attaches middle carbon terminal carbon markovnikov rule called markovnikov product markovnikov product product reaction follows markovnikov rule called markovnikov product markovnikov addition markovnikov addition addition reaction follows markovnikov rule producing markovnikov product anti markovnikov addition certain reactions produce opposite markovnikov product yielding called anti markovnikov product hydrogen ends substituted carbon double_bond hydroboration oxidation reaction ll discuss shortly example reactions conducted peroxides modernized version markovnikov rule explains anti markovnikov behavior original markovnikov rule predicts hydrogen electrophile added double_bond end carbon hydrogens generalizing electrophiles electrophile ends carbon greatest number hydrogens usually hydrogen plays role electrophile hydrogen act nucleophile reactions following expansion markovnikov rule versitile alkene undergoes electrophilic addition electrophile adds carbon greatest number hydrogen substituents nucleophile adds highly substituated carbon simply species adds adds carbon greatest number hydrogens fact reactions reliably produce anti markovnikov products actually powerful tool organic_chemistry example reactions discuss ll different_ways creating alcohols alkenes oxymercuration reduction hydroboration oxidation oxymercuration produces markovnikov product hydroboration produces anti markovnikov product gives organic chemist choice products having stuck single product desired works markovnikov rule works stability carbocation intermediates experiments tend reveal carbocations planar molecules carbon substituents vacant orbital perpendicular rd plane orbital extends trisubstituent plane leads stabilizing effect called happens unfilled antibonding vacant orbital filled bond orbital result filled orbital interacts unfilled orbital stabilizes molecule highly substituted molecule chances stable molecule stabilizing effect inductive effect exceptions rule exceptions markovnikov rule tremendous importance organic synthesis hbr hydrogen peroxide formation free radicals mechanism reacts alkyl free radical forms middle atom stable hydrogen attaches note hydrogen addition second step unlike example addition reactions hydroboration hydroboration useful reaction alkenes end product intermediate product reactions primary ll discuss hydroboration oxidation reaction actually hydroboration reaction followed completely separate oxidation reaction hydroboration mechanism addition bh concerted reaction bonds broken formed time hydroboration happens called syn addition boron hydrogens attach alkene time transition state center image produces sort box alkene carbons boron hydrogen final step boron hydrogens remains attached carbon hydrogen attaches adjacent carbon description fairly adequate reaction actually continues happen bh continue react alkenes giving bh end complex boron atom attached alkyl groups trialkyl boron complex reactions produce products complex bh thf complex borane reality stable bh boron configuration electrons wants natural state actually creates complex shown left furthermore instead bh complex tetrahydrofuran thf shown image right situation result reactions hydroboration oxidation hydroboration oxidation reaction reagent diborane bh alkenes undergo hydroboration yield alkylboranes oxidation alcohols reaction procedure simple convenient yields exceedingly high products ones difficult obtain alkenes anyother way diborane dimer hypothetical bh borane reactions concern acts bh tetrahydrofuran solvents hydroboration reagent exists monomer form acid base complex solvent hydroboration involves addition double_bond bh following stages bh bhr hydrogen attached doubly bonded carbon boron alkylborane undergo oxidation boron replaced oh stage reaction process hydroboration oxidation permits effect addition carbon carbon double_bond elements oh reaction carried ether commonly tetrahydrofuran diglyme diethylene glycol methyl ether ch och_ch och_ch och diborane commercially available tetrahydrofuran solution alkylboranes isolated simply treated situ alkaline hydrogen peroxide stereochemistry orientation hydroboration oxidation converts alkenes alcohols addition highly regiospecific preferred product exactly opposite formed oxymercuration demercuration direct acid catalyzed hydration hydroboration oxtdation process gives products corresponding anti markovnikov addition water carbon carbon double_bond reaction dimethyl butene illustrates particular advantage method rearrangement occur hydroboration evidently carbonium ions intermediates method complications accompany addition reactions reaction illustrates stereochemistry synthesis hydroboration oxidation involves overall syn addition oxymercuration reduction oxymercuration reduction propene alkenes react mercuric acetate presence water compounds reduction yield alcohols stage oxymercuration involves addition carbon carbon double_bond oh hgoac reduction hgoac replaced reaction sequence amounts hydration alkene widely applicable direct hydration stage process oxymercuration reduction fast convenient takes_place mild conditions gives excellent yields alkene added room_temperature aqueous solution mercuric acetate diluted solvent tetrahydrofuran reaction generally complete minutes organomercurial compound isolated simply reduced situ sodium borohydride nabh mercury recovered ball elemental mercury oxymercuration reduction highly regiospecific gives alcohols corresponding markovnikov addition water carbon carbon doublen bond oxymercuration involves electrophilic addition carbon carbon double_bond mercuric ion acting electrophile absence rearrangement high degree typically anti oxymercuration step argues open carbonium ion intermediate instead proposed formed cyclic mercurinium ion analogous bromonium chloronium ions involved addition halogens olah reported spectroscopic evidence preparation stable solutions mercurinium ions mercurinium ion attacked nucleophilic solvent water present case yield addition product attack prevented structural feature net result anti addition addition halogens attack sn type orientation addition shows nucleophile attached highly substituted carbon free carbonium ion intermediate shall transition state reactions unstable threemembered rings sn character reduction generally stereospecific certain special cases accompanied rearrangement despite stage overall process general stereospecific rearrangements occur common reaction dimethyl butene illustrates absence rearrangements typical intermediate carbonium ions diels alder reaction diels alder reaction reaction specifically cycloaddition conjugated diene substituted alkene commonly termed dienophile form substituted cyclohexene reaction proceed atoms newly formed ring carbon diels alder reactions reversible decomposition reaction cyclic called retro diels alder diels alder butadiene ethylene diels alder reaction generally considered useful reactions organic_chemistry requires little energy create cyclohexene ring useful organic reactions concerted single step mechanism certainly involved new carbon carbon bonds partly formed transition state necessarily extent diels alder reaction important example cycloaddition reaction involves electrons diene electrons dienophile known cycloaddition catalytic addition hydrogen catalytic hydrogenation alkenes produce corresponding alkanes reaction carried pressure presence metallic catalyst common industrial catalysts based platinum nickel palladium laboratory syntheses raney nickel formed alloy nickel aluminium employed catalytic hydrogenation ethylene yield ethane proceeds thusly ch_ch catalyst ch_ch electrophilic addition addition reactions alkenes follow mechanism electrophilic addition example prins reaction electrophile carbonyl group halogenation addition elementary bromine chlorine alkenes yield vicinal dibromo dichloroalkanes respectively decoloration solution bromine water analytical test presence alkenes ch_ch br brch_ch br reaction works high electron density double_bond causes temporary shift electrons br br bond causing temporary induced dipole makes br closest double_bond slightly positive electrophile addition hydrohalic acids like hcl hbr alkenes yield corresponding haloalkanes example type reaction ch_ch ch hbr ch_chbr ch carbon atoms double_bond linked different number hydrogen atoms halogen preferentially carbon hydrogen substituents markovnikov rule addition carbene carbenoid yields corresponding cyclopropane oxidation alkenes oxidized large_number oxidizing agents presence oxygen alkenes burn bright flame carbon_dioxide water catalytic oxidation oxygen reaction percarboxylic acids yields epoxides reaction ozone ozonolysis leads breaking double_bond yielding aldehydes ketones ch_ch cho cho reaction determine position double_bond unknown alkene polymerization polymerization alkenes economically important reaction yields polymers high industrial value plastics polyethylene polypropylene polymerization proceed free radical ionic mechanism substitution elimination reaction mechanisms nucleophilic substitution reactions nucleophilic substitution reactions sn sn closely_related elimination reactions discussed later section generally good_idea learn reactions parallels reaction mechanism preferred substrates reactions compete important understand substitution elimination reactions associated specific compound mixture representation certain reactions place times combinations mechanisms occur reaction compete influences solvent nucleophile choice determining factor reaction dominate note notation sn sn stands substitution takes_place stands nucleophilic nucleophile displaces nucleophile stands unimolecular concentration kind molecule determines rate reaction stands bimolecular concentration types molecules determine rate reaction nucleophilic substitution nucleophile attacks molecule takes_place nucleophile leaves nucleophile leaves called leaving group nucleophilic substitutions require nucleophile lewis base electrophile leaving group leaving group charged neutral moiety group breaks free sn vs sn main differences sn sn sn reaction step reaction initiated disassociation leaving group sn reaction hand step reaction attacking nucleophile higher affinity stronger bonding carbon forces_leaving group leave things happen single step different mechanisms explain difference reaction rates sn sn reactions sn reactions dependent leaving group disassociating carbon rate limiting step reaction rate order reaction rate depends solely step alternatively sn reactions single step nucleophile coming reactant opposite leaving group key rate rate dependent concentration nucleophile concentration reactant higher concentrations frequent collisions reaction rate second order reaction nu attacking nucleophile sn reactions primarily things affect sn reaction place important structure alkyl halide methyl primary secondary tertiary carbon components determine sn reaction place nucleophilicity nucleophile solvent reaction reactivity structure sn ch rch_chx cx structure alkyl halide great effect mechanism ch rch preferred structures sn chx undergo sn proper conditions cx rarely involved sn reactions sn nucleophilic substitution bromine generic nucleophile reaction takes_place nucleophile attacking opposite bromine atom notice bonds pointed away bromine attacking nucleophile bonds hydrogen bonds little steric hinderance approaching nucleophile number groups increases steric hinderance making difficult nucleophile close carbon expel bromine atom fact tertiary carbons cx sterically hindered prevent sn mechanim taking place case example secondary carbon great_deal steric hinderance sn mechanism happen depend entirely nucleophile solvent sn reactions preferred methyl halides primary halides important point mind seen clearly example sn reaction molecule undergoes inversion bonds attached carbon pushed away nucleophile approaches transition state bonds planar carbon bromine leaves nucleophile bonds carbon bonds fold away nucleophile particularly important chiral pro chiral molecules configuration converted configuration vice_versa ll contrast results sn reactions examples oh ch cl ho ch cl oh nucleophile cl electrophile hoch product cl leaving group na ch br ch na br reaction taking place acetone solvent sodium iodide disassociate completely acetone leaving iodide ions free attack ch br molecules negatively charged iodide ion nucleophile attacks methyl bromide molecule forcing negatively charged bromide ion taking place bromide ion leaving group nucleophilicity nucleophilicity rate nucleophile displaces_leaving group reaction generally nucleophilicity stronger larger polarizable stable nucleophile specific number unit measure things equal nucleophiles generally compared terms relative reactivity example particular strong nucleophile relative reactivity particular weak nucleophile relationships generalities things_like solvent substrate affect relative rates generally good guidelines species best nucleophiles nucleophiles_lewis bases sn reactions preferred nucleophile strong nucleophile weak base examples rs br cn alternatively strong nucleophile strong base work mentioned earlier text reaction mechanisms compete case strong nucleophile strong base sn mechanism compete mechanism examples strong nucleophiles strong bases include ro oh list descending br cl seh oh leaving group leaving group group substrate leaves case alkyl halide halide ion leaves carbon atom nucleophile attacks tendency nucleophile leave relative reactivity leaving groups br cl fluoride ions poor leaving groups bond strongly rarely alkyl halide substitution reactions reactivity leaving group related basicity stronger bases poorer leaving groups solvent solvent play important role sn reactions particularly sn involving secondary alkyl halide substrates determining factor mechanism solvent great effect reaction rate sn reactions sn mechanism preferred solvent aprotic polar solvent solvent polar polar hydrogen polar protic solvents include water alcohols generally solvents polar nh oh bonds good aprotic polar solvents hmpa ch cn dmso dmf polar solvent preferred better allows dissociation halide alkyl group protic solvent polar hydrogen forms cage hydrogen bonded solvent nucleophile hindering approach substrate relative reactivity solvents hmpa ch cn dmf dmso sn reactions sn mechanism different sn mechanism preferences exactly opposite cases results reaction significantly different like sn mechanism structure plays important role sn mechanism role structure sn mechanism different reactivity structures reversed reactivity structure sn ch_chx cx sn mechanism preferred tertiary alkyl halides depending solvent preferred secondary alkyl halides sn mechanism operate primary alkyl halides methyl halides understand let_look sn mechanism works sn nucleophilic substitution generic halide water molecule produce alcohol diagram step spontaneous dissociation halide alkyl halide unlike sn mechanism attacking nucleophile causes halide leave sn mechanism depends ability halide leave requires certain conditions particular stability carbocation crucial ability halide leave know tertiary carbocations stable best candidates sn mechanism appropriate conditions secondary carbocations operate sn mechanism primary methyl carbocations stable allow mechanism happen halide dissociated water acts nucleophile bond carbocation sn reactions inversion caused nucleophile attacking opposite halide bonded carbon sn mechanism halide left bonds carbon planar water molecule free attack results primarily racemic mixture final step hydrogens bonded water molecule attacked water molecule leaving alcohol note racemic mixtures imply entirely equal amounts mixture rarely case sn slight tendency attack opposite halide result steric hinderence leaving halide close leaving block nucleophile approach solvent like sn mechanism sn affected solvent structure reasons differ sn mechanism polar protic solvent polarity solvent associated dielectric constant solvent solutions high dielectric constants better able support separated ions solution sn reactions concerned polar hydrogen atoms caging nucleophile happens polar protic solvent sn reactions worry mind mechanism reaction step importantly rate limiting step sn reaction ability create stable carbocation getting halide anion leave polar protic solvent polar aprotic solvent creating stable cation polar hydrogens stabilize halide anion better able leave improving rate limiting step goal caging nucleophile unrelated rate limiting step caged state second step attack nucleophile faster step caging simply ignored summary sn sn reaction mechanisms reactions mechanisms number_different reactions usually organic_chemistry goal synthesize product cases possibly competing mechanisms particularly case sn reaction competing dominating mechanism going decide product knowing mechanisms conditions favor determine product cases knowing mechanism allows set environment favorable mechanism mean difference having product minutes ice age designing synthesis product need consider want product options know options ve decided reaction need consider mechanism reaction ask create conditions going happen correctly happen quickly elimination reactions nucleophilic substitution reactions elimination reactions share lot common characteristics sn sn reactions compete products different important understand understanding kinds mechanisms difficult product desire reaction addition sn sn reactions referenced bit way comparison contrast probably best read section continue elimination reactions mechanisms creating alkene products haloalkane reactants elimination unlike sn sn substitution mechanisms occur methyl halides reaction creates double_bond carbon atoms methylhalides carbon note notation stands elimination stands unimolecular concentration kind molecule determines rate reaction stands bimolecular concentration types molecules determine rate reaction vs reaction rates different pathways creating alkenes haloalkanes sn sn reactions key differences reaction rate provides great insight mechanisms reactions like sn reactions step reactions like sn reactions rate limiting step dissociation halide alkane making order reaction depending concentration haloalkane reaction rate hand reactions like sn reactions step reactions sn reactions rate limiting step ability nucleophile attach alkane displace halide second order reaction depends concentrations nucleophile haloalkane reaction rate nu attacking nucleophile zaitsev rule zaitsev rule spelled saytzeff states elimination reaction multiple products possible stable alkene major product highly substituted alkene alkene non hydrogen substituents major product reactions produce mixture products possible generally follow zaitsev rule ll reactions follow zaitsev rule reliably tend produce purer product reaction bromo methylbutane image represents possible pathways bromo methylbutane potential products methylbut ene methylbut ene images right simplified drawings molecular product shown images center left bromine second carbon reaction hydrogen removed st rd carbon zaitsev rule says hydrogen removed predominantly rd carbon reality mixture product methylbut ene mechanism reaction ll later necessarily case reactivity structure rch_chx cx mechanism concerted higly stereospecific occur leaving group anti coplanar position newman projection anti configuration behaviour stems best overlap orbitals adjacent carbons pi bond formed leaving group brought position structure molecule mechanism place mechanism elimination note anti coplanarity atoms molecules having accessible anti coplanar conformations react route furthermore mechanism operate contrary zaitsev rule anti coplanar hydrogen leaving group results stable alkene good_example happen looking cyclohexane cyclohexene derivatives operate conditions preferential elimination let_look example reactant chloro drawing left conformation drawing ring flip center newman projections conformations drawings right products assume treating chloro strong base example ch_ch ethanolate mechanism dominates hydrogens carbons adjacent chlorinated carbon red green ones hard attached carbon red hydrogen angled little plane viewer red hydrogen hydrogen chlorine atom eligible mechanism product going ene notice contrary zaitsev rule says substituted alkene preferred rule primary product leave substituted alkene simply produced steric hindrance images shows molecule ring flip conformation product possible newman projection hydrogens chlorine atom important considering mechanism understand geometry molecule geometry advantage preferentially single product times prevent getting product want ll_need consider different mechanism product note word periplanar instead coplanar coplanar implies precisely degree separation peri greek near implies near degrees periplanar actually accurate case chloro example molecular forces chlorine atom actually slightly degrees hydrogen isopropyl group case periplanar correct term elimination alkyl halide base mechanism begins dissociation leaving group alkyl producing carbocation alkyl group leaving anion way sn reaction begins thing helps initiate step sn reactions help initiate step reactions specifically secondary tertiary carbocations preferred stable primary carbocations choice solvent sn polar protic solvent preferred polar aspect stabilizes carbocation protic aspect stabilizes anion makes difference reaction takes sn pathway depend second step action nucleophile sn reactions strong nucleophile weak base preferred nucleophile attack bond carbocation reactions strong nucleophile preferred difference strong nucleophile strong base causes nucleophile attack hydrogen carbon instead carbocation nucleophile base extracts hydrogen causing bonding electrons fall produce pi bond carbocation hydrogen leaving group lost separate steps fact requirements geometry mechanism reliably produces products follow zaitsev rule references

In [82]:

    

print wiki_colloc.bigrams.pattern.replace('|','\n')[:500]


    

    




(invisibility cloak
rob horning
deathly hallows
atlas shrugged
prisoner azkaban
bile duct
cellular automata
biol phys
spinal cord
vice versa
radical prostatectomy
cleft palate
console writeline
deploy plugins
hospital wing
barset skip
chamber secrets
ff ff
autosomal dominant
două sute
radiat oncol
tom riddle
oncol biol
oo oo
baking soda
bie deploy
mental retardation
clin oncol
amino acids
totalt drwxr
drwxr xr
supreme court
multo ben
philosopher stone
media noche
soviet union
lemon juice
prime m

In [ ]:

    




    

In [ ]:

    




    

In [ ]:

    




    

In [ ]:

    




    

In [ ]:

    




    

In [ ]:

    




    

In [ ]:

    




    

In [ ]:

    




    

In [2]:

    

# Code for setting the style of the notebook
from IPython.core.display import HTML
def css_styling():
    styles = open("../theme/custom.css", "r").read()
    return HTML(styles)
css_styling()


    

    
Out[2]: