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5KeyFactorsThatAffectAcidityinOrganicChemistryMasterOrganicChemistry

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FiveKeyFactorsThatInfluenceAcidity
byJames
inAlcohols,Alkanes,Alkenes,Alkynes,Carboxylicacids,ChemicalBonds,Esters,FunctionalGroups,
Ketones,OrganicChemistry1,UnderstandingElectronFlow,WhereElectronsAre
IvewritteninschoolmarmishtonesbeforeabouthowpKaisoneofthemostimportantmeasuresyou
canlearninorganicchemistry,andnotknowingsomebasicpKavaluesbeforeanexamisalotlike
walkinguptoapokertablewithoutknowingthevaluesofthehands:youregoingtoloseyourshirt.
Todaywelltalkaboutwhatsbehindthetrendsinacidityfordifferentmoleculesanddiscussthemost
importantfactorsthatdeterminethesevalues.Beforewegetstarted,however,letsquicklyreviewthe
basicsofacidityandbasicity.Heresthecondensedversion:
1. Bronstedacidsareprotondonors,Lewisacidsareelectronpairacceptors.Converse:Bronsted
base=protonacceptor,Lewisbase=electronpairdonor.
2. Aconjugatebaseiswhatyouobtainwhenyouremoveaproton(H+)fromacompound.For
instance,HO()istheconjugatebaseofwater.O(2)istheconjugatebaseofHO().Conversely,
conjugateacidsarewhatyouobtainwhenyouaddaprotontoacompound.Theconjugateacidof
waterisH3O(+).
3. Quickquiz:ispH1acidicorbasic?pKaissimilartopHinthatlow(andevennegativevalues)
denotestrongacids.ThatsbecausepKaisbasedontheequilibrium:
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4. Accordingtothis,anythingwhichstabilizestheconjugatebasewillincreasetheacidity.
ThereforepKaisalsoameasureofhowstabletheconjugatebaseis.Putanotherway,strongacids
haveweakconjugatebases,andviceversa.
Withthatoutoftheway,letsgetstarted.
Factor#1Charge.
Removalofaproton,H+,decreasestheformalchargeonanatomormoleculebyoneunit.Thisis,of
course,easiesttodowhenanatombearsachargeof+1inthefirstplace,andbecomesprogressively
moredifficultastheoverallchargebecomesnegative.Theaciditytrendsreflectthis:

Notethatonceaconjugatebase(B)isnegative,aseconddeprotonationwillmakethedianion(B2).
Whilefarfromimpossible,formingthedianioncanbedifficultduetothebuildupofnegativechargeand
thecorrespondingelectronicrepulsionsthatresult.
Factor#2TheRoleoftheAtom
Thispointcausesalotofconfusionduetothepresenceoftwoseeminglyconflictingtrends.
Heresthefirstpoint:acidityincreasesaswegoacrossarowintheperiodictable.Thismakessense,
right?ItmakessensethatHFismoreelectronegativethanH2O,NH3,andCH4duetothegreater
electronegativityoffluorineversusoxygen,nitrogen,andcarbon.Afluorinebearinganegativechargeis
ahappyfluorine.
Butherestheseeminglystrangething.HFitselfisnotastrongacid,atleastnotinthesensethatit
ionizescompletelyinwater.HFisaweakeracidthanHCl,HBr,andHI.Whatsgoingonhere?

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Youcouldmaketwoargumentsforwhythisis.Thefirstreasonhastodowiththeshorter(andstronger)
HFbondascomparedtothelargerhydrogenhalides.Thesecondhastodowiththestabilityofthe
conjugatebase.Thefluorideanion,F()isatinyandviciouslittlebeast,withthesmallestionicradiusof
anyotherionbearingasinglenegativecharge.Itschargeisthereforespreadoverasmallervolumethan
thoseofthelargerhalides,whichisenergeticallyunfavorable:foronething,F()begsforsolvation,
whichwillleadtoalowerentropytermintheG.
NotethatthistrendalsoholdsforH2OandH2S,withH2Sbeingabout10milliontimesmoreacidic.
Factor#3Resonance.
Ahugestabilizingfactorforaconjugatebaseisifthenegativechargecanbedelocalizedthrough
resonance.Theclassicexamplesarewithphenol(C6H5OH)whichisaboutamilliontimesmoreacidic
thanwater,andwithaceticacid(pKaof~5).

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Watchoutthoughitisntenoughforasystemtosimplybeadjacenttoaprotontheelectronsofthe
conjugatebasehavetobeinanorbitalwhichallowsforeffectiveoverlap(foradastardlytrickquestion
inthisveinthatroutinelystymiesHarvardpremeds,lookhere.)
Factor#4Inductiveeffects.Electronegativeatomscandrawnegativechargetowardthemselves,
whichcanleadtoconsiderablestabilizationofconjugatebases.Checkouttheseexamples:

Predictably,thiseffectisgoingtoberelatedtotwomajorfactors:1)theelectronegativityoftheelement
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(themoreelectronegative,themoreacidic)andthedistancebetweentheelectronegativeelementandthe
negativecharge.
Factor#5Orbitals.Again,theacidityrelatesnicelytothestabilityoftheconjugatebase.Andthe
stabilityoftheconjugatebasedependsonhowwellitcanaccomodateitsnewfoundpairofelectrons.In
aneffectakintoelectronegativity,themorescharacterintheorbital,theclosertheelectronswillbeto
thenucleus,andthelowerinenergy(=stable!)theywillbe.

LookatthedifferencebetweenthepKaofacetyleneandalkanes25!Thats10tothepowerof25,as
in,100timesbiggerthanAvogadrosnumber.Justtogiveyouanideaofscale.Thatstheamazing
thingaboutchemistrythesheerrangeinthepowerofdifferentphenomenaisaweinspiring.
TheresactuallyamnemonicIvefoundthatcanhelpyouremembertheseeffects.ThisiscreditedtoDr.
ChristinePruis,SeniorLectureratArizonaStateUniversityTempe.
Charge
Atom
Resonance
DipoleInduction
Orbitals
=CARDIO.
Treadcarefullywithmnemonics,butthereyougo.

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Taggedas:acidity,acids,bases,basicity,chargestability,conjugateacid,conjugatebase,dipoles,
electronegativity,hybridization,polarizability,resonance
{45commentsreadthembeloworaddone}

HeeroFongJanuary12,2011at12:54pm
Ijustwantedtosayyouaredoinganabsolutelyfantasticjobofteachingorganicchemistryand
makingitcomprehensible.Ivebeenreadingyourpostsforthelastfewdays,andmaterialwhich
wasalientomebeforeasfinallystartedtomakesense.
Thanks!
Reply

JamesJanuary12,2011at7:09pm
Thanks!
Reply

howaidajouniMarch12,2011at4:19pm
thanksformakingorgchemistryeasierbutihaveaquestionaboutresonance,youdidntmention
http://www.masterorganicchemistry.com/2010/09/22/fivekeyfactorsthatinfluenceacidity/

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electrondonationorwithdrawalbyresonance
Reply

JamesMarch13,2011at1:32pm
Thatsathornyissueitcanbehardtoseparatetheinfluenceofinductiveandresonance
effects.Doyouhaveaspecificexamplethatyourethinkingof?
Reply

AliOctober19,2011at2:36am
Iwasthemostconfusedpersonwhocouldnotunderstandtheconcept.Ireadyournote.Ireceived
100%onAciditypartonmyExam.Thankyou!
Reply

jamesOctober19,2011at3:10am
Thisisthekindofcommentthatmakesmyday.Thanks!
Reply

PatNovember5,2011at12:03am
IlovethissiteIhatereadingorganicchemtxtbooksbecausemostareboooooringbutyoumake
studyingforOchemthehighlightofmyfridayeveningYouarefunny,andyourdeliverystyle
isabsolutelyamazing!!IaminOchemII,barelymadeitthroughthefirstbutIamexcellinginmy
second.Thankyousirfordoingthis!!IappreciateitmorethanyouknowGoodday!
Reply

LaraFebruary14,2012at1:24am
Thankyousomuchforthissummarysheet,Iwashavingsomuchtroubletryingtofigureoutwhat
madeamoleculemoreacidicandhereitallis!Fullyexplainedandeasilyunderstandable.
Fantasticstuff.
Reply

LainaMarch12,2012at7:06pm
http://www.masterorganicchemistry.com/2010/09/22/fivekeyfactorsthatinfluenceacidity/

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Ijustwantedtothankyouforalltheworkyouputintothissite.ImanundergraduateatYaleand
forthepastsemester,IvebeenafraidIllfailOrgo.Thankstoyoursite,Inolongerfeelasstressed
becauseyouvedonesuchagoodjobofexplainingthings.So,yes,thankyou!!
Wishingyouthebest!
Reply

jamesMarch13,2012at8:56am
ThanksLaina.Gladyoufindituseful.LetmeknowiftheresanythingIcandotomakethe
sitemorehelpfulforyourneeds.
Reply

AlaMarch22,2012at6:03pm
IhaveaproblemwhereIhavetodeterminethemoststableconjugatebase,whichindicatesthe
strongestacid.Ijustwanttoknow,isitpossibletohaveastrongacidaccordingtoitspKavalue,
butaccordingtoatom,resonance,etc.anotheracidisstronger?
Reply

jamesMarch23,2012at5:31pm
pKarepresentsanexperimentalmeasurement.Experimentalmeasurementsareprimarythe
conceptswepulloutofthem,suchasthefactorsmentioned,aresecondary.Sowhatyoure
mentioningisntpossible,assumingallothervariablesarethesame.
Reply

MarianaApril24,2012at7:27pm
Ijustdontseemtounderstandwhydoesionicradiusincreaseacidity?Imean,BindingEnergy
decreasesanditsmoreeasytoloseanelectron,ifacidsarecompoundsthatacceptelectronshow
doesacidityincrease?
Reply

jamesApril26,2012at8:16pm
Basicityisallaboutthestabilityofnegativecharge.Withlargeratoms,essentiallythe
chargeismorespreadoutoveragreatervolume.Lowerchargedensitiesaremorestable.
Seealsohere:http://masterorganicchemistry.com/2012/04/25/walkthroughofacidbase
http://www.masterorganicchemistry.com/2010/09/22/fivekeyfactorsthatinfluenceacidity/

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reactions3aciditytrends/
Reply

NaomiBowensJune2,2012at3:44am
Ifeelsooomuchmoreconfidentaboutorgobcofu=)
Reply

GuvanthiJuly29,2012at5:03pm
Allthesestuffwereveryusefultome.GottoknowmorethingsthatIdidntknowbefore.Thanks
alot..!Similararticleonbasicitywillbeappreciatedalot..!
Reply

TomAugust1,2012at7:22pm
OnthefiguredescribinginductiveeffectsonpKaofcarboxylicacidsyouhavebromoaceticacid
withpKaof2.86ononelineand2.97onthenext.Whythedifference?
Reply

jamesAugust6,2012at9:57pm
Fixed.ThanksforthespotEvanspKatablesays2.86.NotsurewhereIpulledthe2.97
from.
Reply

LuisSanchezSeptember7,2012at12:05am
Thissiteissohelpful.Itmakesorganicchemistrywayeasier.Thankyou!
Reply

jamesSeptember8,2012at7:11pm
GladyoufindithelpfulLuis.
Reply
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streaSeptember12,2012at5:34pm
Ohwow,thisisamazing.Iwasstartingtothinktherewasnosite/bookthathadexactlythis
information,thiscompactly(andbrilliantly,mightIadd)presented.Thankyousomuch!Youve
gotnoideahowmuchthishelped(andhowmuchitreducedmystudytime,godknowswecanall
dowithextratimeonourhands:)).Thanksagain!
Reply

YashFebruary20,2013at10:25pm
Thisisawesome:D!Ineverquitegotaholdofthistopicsincethepast23monthsandnowafter
readingthispageitsallcrystalcleartome!Andasforthemnemonic,whenitoldittomychem
teacher,hewasimpressedandaskedmeforthewebsite:D!Greatjob,keepitup:D
Reply

jamesFebruary22,2013at3:59pm
Great,gladyoufoundituseful!
Reply

AnnieMarch1,2013at7:41pm
CanyoupleasemakethesenotesavailableasPDF?
Thanks.
Reply

AkashSharmaApril16,2013at2:38am
youcanuseweb2pdfforthat
googleit
italsohasbrowserplugin..
Reply

AkashSharmaApril16,2013at2:34am
Organicismyfavouritepartinchemistry.Yourpostandcontentsprovidedmeagoodquick
http://www.masterorganicchemistry.com/2010/09/22/fivekeyfactorsthatinfluenceacidity/

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revisionbeforemyexamsandIdidextremelywell..
Thankstoyou.youhaveagoodwayofteachingorganicchemistry..
Iwoulddefinitelyrecommendthissitetomyfriendswhothinkorganicisboaringsubject.
Onceagainthanks..
Reply

ChrisJune12,2013at10:42am
IamcurioushowyoucameupwiththisCARDIOacronym?Andwhen?Ihavehearditfromone
otherpersonafewyearsago.
Reply

jamesJune19,2013at9:04pm
IshamelesslystoleitfromacommentthreadonSDN.
Reply

PegahBiparvaJune12,2013at6:53pm
DidyougettheCARDIOacronymfromaDr.ChristinePruisorChadsReviewsfromArizona
StateUniversity?Dr.PruisisourOrganicChemistryprofessorandcameupwiththisacronym78
yearsago,soperhapsthatisthecredityouspeakof?Ifso,thatisawesome!
Reply

EmilySeptember23,2013at3:26pm
ThiswasreallyclearandhelpfulThankyousomuch!!
Reply

JamesAshenhurstSeptember24,2013at10:30pm
Awesome,gladtohearit.
Reply

vickyOctober28,2013at10:18am
http://www.masterorganicchemistry.com/2010/09/22/fivekeyfactorsthatinfluenceacidity/

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ididntget5pointorbitalasscharacterincreasesthentshouldbesp3<
sp2<sp
Reply

HamzaJanuary16,2014at8:09pm
Whentryingtochooseacompoundswiththehighestacidity,accordingtoCARDIO,howdoyou
determinewhichfactoryoushouldprioritizefirst?
Forexample:
Supposeyouretryingtodeterminewhichcompoundismoreacidic,CHCHorbenzenering?
WhenyouremovetheprotonthebenzeneringisstabilizedbyresonancebuttheHCChasalotof
scharacterinitsorbital.Howwouldyoudeterminewhichcompoundismoreacidic?
Reply

nicholeMarch6,2014at9:42am
Justwantedtosincerelythankyoufortransforminganextremelydifficultsubjectintosomething
comprehensibleandfuthermoreenjoyable.Theressomethingtobesaidforthatspecifictalentand
itisgreatlyappreciated.Youruseofacronymsanddescriptivecontexthaveimprovedbothmy
labsandtestmarks.
Thankyou.
Reply

MariahMarch12,2014at8:56pm
dolonepairscountwhenfiguringoutthehybridizationofanorbital?
Reply

MariahMarch12,2014at9:08pm
andforfactor#5dowelookatthehybridizationoftheacidortheconjugatebase?
ex//ch3hasahybridizationorbitalofsp3butitsCBch2hasahybridizationofsp2
Reply

muhammadshahrozApril14,2014at4:37pm
Fantastic!Whatanexplanation.Truelyhelpfulandadmirable.
Reply
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EmMay5,2014at6:49pm
Thankyousomuch!Lovereadingthrougheverything!Youmakeitsounderstandableand
interesting!Ireallyappreciatethelinkstomoretopicstoo!
Reply

mydoubts2May31,2014at4:01am
whyisOHmorebasicthanSH.isminussign
Reply

KikiJune3,2014at4:17pm
Thankyousomuch!!YouhavemademyMCATstudyingmorealightjog)
Reply

LauraAugust3,2014at10:10pm
WhyisitthatHFismoreacidicthanHI(#2),butwhenitsconnectedtothecarboxylgroupitisI
thatismoreacidic?Anyone?
Reply

BrandonSeptember26,2014at4:51pm
Hey!Thesepageshavebeengreat,wherecanwefindtheanswerstotheproblemsyouusually
giveattheend?
Reply

SidraNovember5,2014at3:33pm
whystaboilizationofconjugatebaseenhanceacidity?
Reply

JamesNovember6,2014at11:46am
http://www.masterorganicchemistry.com/2010/09/22/fivekeyfactorsthatinfluenceacidity/

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Equilibriumtendstoproceedtowardthemorestableproduct,yes?Sowhathappenstothe
equilibriumHA>H+AasyoumakeAmorestable?
Reply

HannahNovember7,2014at2:23pm
thiswassohelpfulthankyou!
Reply
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Imaginehavingacomprehensiveonlineguidetohelpyousolveyourown
problemsinorganicchemistry.That'smymissionwiththissite.Afterearninga
Ph.D.atMcGillanddoingapostdocatMIT,Iappliedtobeaprofessor.That
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ConversionofcarboxylicacidsintoacidchlorideswithSOCl2
Conversionofcarboxylicacidstocarboxylatesusingbase
Conversionofcarboxylicacidstoestersusingacidandalcohols(FischerEsterification)
ConversionoftertiaryalcoholstoalkylbromidesusingHBr
ConversionoftertiaryalcoholstoalkyliodideswithHI
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FriedelCraftsacylationofaromaticgroupstogiveketones
HalogenationofAlkynes
HellVollhardZelinskyReaction
Hofmanneliminationofalkylammoniumsaltstogivealkenes
HofmannRearrangementofAmidestoAmines
HydroborationofAlkenes
HydroborationofalkynesusingBH3togivealdehydes
HydrogenationofAlkenestogiveAlkanes
HydrogenationofAlkynestoAlkanesusingPd/C
Hydrolysisofacetalstogivealdehydesandketones
Hydrolysisofesterstocarboxylicacidswithaqueousacid
Hydrolysisofiminestogiveketones(oraldehydes)
Hydrolysisofnitrileswithaqueousacidtogivecarboxylicacids
Iodinationofalkenestogivevicinaldiiodides(1,2diiodides)
IodinationofAromaticswithI2
Ketoenoltautomerism
KilianiFischerSynthesis
Nitrationofaromaticgroups
NucleophilicAromaticSubstitution(SNAr)
NucleophilicAromaticSubstitutionViaArynes
Openingofepoxideswithacidandwatertogivetransdiols
Openingofepoxideswithnucleophilesunderacidicconditions
OxidationofaldehydestocarboxylicacidsusingCr(VI)
OxidationofaldehydestocarboxylicacidswithAg2O
OxidationofaromaticalkaneswithKMnO4togivecarboxylicacids
Oxidationofprimaryalcoholstoaldehydes
OxidationofPrimaryAlcoholstoAldehydesusingPCC
Oxidationofprimaryalcoholstocarboxylicacids
OxidationofsecondaryalcoholstoketonesusingPCC
Oxidationofthiolstodisulfides
Oxidativecleavageof1,2diolstogivealdehydes/ketones
Oxidativecleavageofalkenestogiveketones/carboxylicacidsusingozone(O3)
(oxidativeworkup)
Oxidativecleavageofalkenestoketones/carboxylicacidsusingKMnO4
OxidativeCleavageofAlkyneswithKMnO4
OxidativeCleavageofAlkyneswithOzone(O3)
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OxymercurationofAlkenestoformEthersusingHg(OAc)2
OxymercurationofAlkynes
Oxymercuration:AlcoholsfromalkenesusingHg(OAc)2andWater
Ozonolysisofalkenestoketonesandaldehydes(reductiveworkup)
Partialreductionofalkynestotransalkenesusingsodiumandammonia
PartialreductionofalkyneswithLindlarscatalysttogivecisalkenes
PinacolRearrangement
Polymerizationofdieneswithacid
Protectionofalcoholsassilylethers
Protonationofalcoholstogiveoxoniumions
ProtonationofGrignardreagentstogivealkanes
Reactionofalkylhalideswithwatertoformalcohols(SN1)
Reactionofepoxideswithnucleophilesunderbasicconditions
ReactionsofDiazoniumSalts
ReductionofaromaticketonestoalkaneswithPd/Candhydrogen
Reductionofaromaticnitrogroupstoaminogroups
ReductionofcarboxylicacidstoprimaryalcoholsusingLiAlH4
ReductionofesterstoaldehydesusingDIBAL
ReductionofesterstoprimaryalcoholsusingLiAlH4
ReductionofnitrilestoprimaryamineswithLiAlH4
ReductiveAmination
SharplessEpoxidation
SN2ofCyanidewithAlkylHalidestogiveNitriles
SN2reactionbetweenazideionandalkylhalidestogivealkylazides
SN2ReactionofAcetylideIonswithAlkylHalides
SN2reactionofalkoxideionswithalkylhalidestogiveethers(Williamsonsynthesis)
SN2reactionofalkylhalideswithhydroxideionstogivealcohols
SN2reactionofamineswithalkylchloridestogiveammoniumsalts
SN2reactionofcarboxylateionswithalkylhalidestogiveesters
SN2reactionofhydrosulfideionwithalkylhalidestogivethiols
SN2reactionoforganocuprates(Gilmanreagents)withalkylhalidestogivealkanes
SN2reactionofthiolateswithalkylhalidestogivethioethers(sulfides)
SN2reactionofwaterwithalkylhalidestogivealcohols
StilleReaction
Substitution(SN1)withhydrideshift
Substitutionwithaccompanyingalkylshift
SulfonylationofArenestogivesulfonicacids
SuzukiReaction
TheGabrielsynthesisofamines
Thehaloformreaction:conversionofmethylketonestocarboxylicacids
TheHeckReaction
TheMalonicEsterSynthesis
TheMannichReaction
TheRobinsonAnnulation
Transesterificationpromotedbyalkoxides
WittigReactionconversionofketones/aldehydestoalkenes
WolffKishnerReactionconversionofketones/aldehydestoalkanes
WolffRearrangement
ReactionGuideCheckoutPage
ResonanceCrashCourse
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5KeyFactorsThatAffectAcidityinOrganicChemistryMasterOrganicChemistry

ResonanceCrashCourseThanks!
ResonanceCrashCourseCheckout
ResonancePracticeExamQuestionsWithSolutions
ResonanceWebinar
ResourceGuide
Resources
ShareYourOrganicChemistrySuccessStory
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SpectroscopyVideoThanks!
StereochemistryCrashCourse
StereochemistryCrashCourse
StereochemistryPracticeExamQuestionsWithSolutions(Beginner/Intermediate)
StereochemistryWebinar
StereochemistryWebinarSundayNov3
StoreAction
StudyandExamTips
SummarySheets
TestPage
testtypg
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Thanks!YoureSignedUpForTheReactionGuide
TheCatLineDiagram
ThoughtsOnOChem
TuesdayOct22AcidBaseWebinarat9pmEST
Videos
ASimpleTrickForDeterminingR/S
ApplyingE2ReactionswithNewmanProjections
BondRotations:Exercise1
BondRotations:Exercise2
BondRotations:Exercise3
BondRotations:Exercise4
BondRotations:Exercise5
BondRotations:TheSteeringWheelAnalogy
BronstedandLewisAcidity
BulkyBasesinEliminationReactions
CarbocationStability
ComparingE1andE2Mechanisms
ComparingE1andE2Stereochemistry
ComparingtheE1andSN1
ComparingtheSN1andSN2
ConvertingaFischerProjectionToALineDiagram
ConvertingaLineDiagramtoaFischerProjection
ConvertingaNewmanProjectiontoaLineDiagram
CurvedArrows
DeterminingR/SonaFischerProjection
E1withRearrangement
E1WithRearrangement(2)
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EliminationExercise:ZaitsevsRule
EliminationReactionsinCyclohexanes
EliminationReactionsinCyclohexanes(2)
EvaluatingResonanceForms(1)Charges
EvaluatingResonanceForms(2)Octets
EvaluatingResonanceForms(3)NegativeCharge
EvaluatingResonanceForms(4)PositiveCharge
EvaluatingResonanceForms(5)Aromaticity
Exercise:CondensedFormula(1)
Exercise:CondensedFormula(2)
FactorsThatAffectAcidity(1)ChargeDensity
FactorsThatAffectAcidity(2)Electronegativity
FactorsThatAffectAcidity(3)Polarizability
FactorsThatAffectAcidity(4)ElectronWithdrawingGroups
FactorsThatAffectAcidity(4)Resonance
FactorsThatAffectAcidity(6)Orbitals
FactorsthataffectacidityAromaticity
FormalCharge(1)AtomicCharge
FormalCharge(2)IntroductiontoFormalCharge
FormalChargeExercise:AllylCarbocation
FormalChargeExercise:CH2N2
FormalChargeExercise:CH3NO2
FormalChargeExercise:CN
FormalChargeExercise:CO3
FormalChargeExercise:HiddenHydrogens
FormalChargeExercise:HiddenLonePairs
FormalChargeExercise:N3
FormalChargeExercise:NH4
FormalChargeExercise:O3
FormalChargeExercise:RadicalsandCarbenes
HiddenHydrogens
HowFormalChargeCanMislead
HowHeatAffectsEliminationReactions
Howtodrawanenantiomer
HowToUseApKaTable
InSummary:Resonance
IntroductiontoElimination
IntroductiontopKa
IntroductiontoRearrangements
IntroductiontoResonance
IntroductiontotheE2Reaction
IntroductiontotheSN1:Experiments
IntroductiontotheSN2:Experiments
KeyPatternsinFormalCharge
LineDrawings
MakingOHIntoAGoodLeavingGroup
RearrangementReactions:AlkylShifts
Rearrangement:HydrideShift
Rearrangements:CarbocationStability
ResonanceCommonMistakes(1)
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ResonanceCommonmistakes(2)
SN1Exercise:TheSubstrate
SN1ReactionEnergyDiagram
SN1vs.SN2Overview
SN1WithAlkylShift(1)
SN1WithAlkylShift(2)
SN1WithHydrideShift
SN1/SN2/E1/E2Substrate
SN1/SN2/E1/E2DecisionOverview
SN1/SN2/E1/E2DecisionSolvent
SN1/SN2/E1/E2DecisionTemperature
SN1/SN2/E1/E2DecisionTheNucleophile/Base
SN1:ApplyingtheSN1Reaction
SN2Exercise:ApplytheSN2
SN2Exercise:LeavingGroups
SN2Exercise:TheSubstrate
SolventsinSN1andSN2Reactions
StereochemistryExercise1
StereochemistryExercise2
StereochemistryExercise3
StereochemistryExercise4
StereochemistryExercise5
StrongandWeakAcids
Substitution:WhatisSubstitution?
The4ComponentsofEveryAcidBaseReaction
TheE1Reaction
TheGoldenRuleofAcidBaseReactions
TheSingleSwapRule
TheSN1Mechanism
TheSN2Mechanism
TheSN2ReactionEnergyDiagram
UnderstandingR/SRelationships
UnequalResonanceForms
UsingElectronegativitytoFindReactiveSitesonaMolecule
WhatMakesAGoodLeavingGroup?
WhatMakesAGoodNucleophile?(1)
WhatMakesAGoodNucleophile?(2)
WhatMakesAGoodNucleophile?(3)
WhatsANucleophile?
ZaitsevsRule

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