ReactionsofAlkenes

AdditionReactionsofAlkenes
Themostcommonchemicaltransformationofacarboncarbondoublebondistheadditionreaction.Alargenumberofreagents,both
inorganicandorganic,havebeenfoundtoaddtothisfunctionalgroup,andinthissectionweshallreviewmanyofthesereactions.A
majorityofthesereactionsareexothermic,duetothefactthattheCCpibondisrelativelyweak(ca.63kcal/mole)relativetothesigma
bondsformedtotheatomsorgroupsofthereagent.Remember,thebondenergiesofamoleculearetheenergiesrequiredtobreak
(homolytically)allthecovalentbondsinthemolecule.Consequently,ifthebondenergiesoftheproductmoleculesaregreaterthanthe
bondenergiesofthereactants,thereactionwillbeexothermic.ThefollowingcalculationsfortheadditionofHBraretypical.Notethat
byconventionexothermicreactionshaveanegativeheatofreaction.

1.AdditionofStrongBrnstedAcids
Asillustratedbytheprecedinggeneralequation,strongBrnstedacidssuchasHCl,HBr,HI&H2SO4,rapidlyaddtotheC=C
functionalgroupofalkenestogiveproductsinwhichnewcovalentbondsareformedtohydrogenandtotheconjugatebaseoftheacid.
Usingtheaboveequationasaguide,writetheadditionproductsexpectedonreactingeachofthesereagentswithcyclohexene.

ShowProducts

WeakBrnstedacidssuchaswater(pKa=15.7)andaceticacid(pKa=4.75)donotnormallyaddtoalkenes.However,theadditionof
astrongacidservestocatalyzetheadditionofwater,andinthiswayalcoholsmaybepreparedfromalkenes.Forexample,ifsulfuric
acidisdissolvedinwateritiscompletelyionizedtothehydroniumion,H3O(+),andthisstronglyacidic(pKa=1.74)specieseffects
hydrationofetheneandotheralkenes.
CH2=CH2+H3O(+)>HCH2CH2OH+H(+)
Theimportanceofchoosinganappropriatesolventfortheseadditionreactionsshouldnowbeclear.IftheadditionofHCl,HBrorHIis
desired,waterandalcoholsshouldnotbeused.ThesestrongacidswillionizeinsuchsolventstogiveROH2(+)andthenucleophilic
oxygenofthesolventwillcompetewiththehalideanionsinthefinalstep,givingalcoholandetherproducts.Byusinginertsolventssuch
ashexane,benzeneandmethylenechloride,thesecompetingsolventadditionsareavoided.Becausetheseadditionsproceedbywayof
polarorionicintermediates,therateofreactionisgreaterinpolarsolvents,suchasnitromethaneandacetonitrile,thaninnonpolar
solvents,suchascyclohexaneandcarbontetrachloride.

RegioselectivityandtheMarkovnikovRule
Onlyoneproductispossiblefromtheadditionofthesestrongacidstosymmetricalalkenessuchasetheneandcyclohexene.However,if
thedoublebondcarbonatomsarenotstructurallyequivalent,asinmoleculesof1butene,2methyl2buteneand1methylcyclohexene,

thereagentconceivablymayaddintwodifferentways.Thisisshownfor2methyl2buteneinthefollowingequation.
(CH3)2C=CHCH3+HCl
2methyl2butene

(CH3)2CHCHClCH3 or (CH3)2CClCHHCH3
2chloro3methylbutane

2chloro2methylbutane

Whenadditionreactionstosuchunsymmetricalalkenesarecarriedout,wefindthatoneofthetwopossibleconstitutionallyisomeric
productsisformedpreferentially.Selectivityofthissortistermedregioselectivity.Intheaboveexample,2chloro2methylbutaneis
nearlytheexclusiveproduct.Similarly,1buteneforms2bromobutaneasthepredominantproductontreatmentwithHBr.

Afterstudyingmanyadditionreactionsofthiskind,theRussianchemistVladimirMarkovnikovnoticedatrendinthestructureofthe
favoredadditionproduct.HeformulatedthistrendasanempiricalrulewenowcallTheMarkovnikovRule:WhenaBrnstedacid,
HX,addstoanunsymmetricallysubstituteddoublebond,theacidichydrogenoftheacidbondstothatcarbonofthedoublebondthat
hasthegreaternumberofhydrogenatomsalreadyattachedtoit.
Inmorehomeliervernacularthisrulemayberestatedas,"Themthathasgits."
Itisahelpfulexercisetopredictthefavoredproductinexamplessuchasthoseshownbelow:

ShowProducts

EmpiricalrulesliketheMarkovnikovRuleareusefulaidsforrememberingandpredictingexperimentalresults.Indeed,empiricalrules
areoftenthefirststeptowardpracticalmasteryofasubject,buttheyseldomconstitutetrueunderstanding.TheMarkovnikovRule,for
example,suggeststherearecommonandimportantprinciplesatworkintheseadditionreactions,butitdoesnottelluswhattheyare.
Thenextstepinachievinganunderstandingofthisreactionmustbetoconstructarationalmechanisticmodelthatcanbetestedby
experiment.
AllthereagentsdiscussedherearestrongBrnstedacidsso,asafirststep,itseemssensibletofind
abasewithwhichtheacidcanreact.Sinceweknowthattheseacidsdonotreactwithalkanes,it
mustbethepielectronsofthealkenedoublebondthatserveasthebase.Asshowninthediagram
ontheright,thepiorbitalextendsintothespaceimmediatelyaboveandbelowtheplaneofthe
doublebond,andtheelectronsoccupyingthisorbitalmaybeattractedtotheprotonofaBrnsted
acid.Theresultingacidbaseequilibriumgeneratesacarbocationintermediate(theconjugateacidof
thealkene)whichthencombinesrapidlywiththeanionicconjugatebaseoftheBrnstedacid.This
twostepmechanismisillustratedforthereactionofethenewithhydrogenchloridebythefollowing
equations.
FirstStep:H2C=CH2+HCl

HH2CCH2(+)+Cl()

SecondStep:HH2CCH2(+)+Cl()

HH2CCH2Cl

Anenergydiagramforthistwostepadditionmechanismisshowntotheleft.Fromthisdiagramweseethatthesloworratedetermining
step(thefirststep)isalsotheproductdeterminingstep(theanionwillnecessarilybondtothecarbocationsite).Electrondonatingdouble
bondsubstituentsincreasethereactivityofanalkene,asevidencedbytheincreasedrateofhydrationof2methylpropene(twoalkyl
groups)comparedwith1butene(onealkylgroup).Evidently,alkylsubstituentsacttoincreasetherateofadditionbyloweringthe
activationenergy,E1oftheratedeterminingstep,anditishereweshouldlookforarationalizationofMarkovnikov'srule.
Asexpected,electronwithdrawingsubstituents,suchasfluorineorchlorine,reducethereactivityofanalkenetoadditionbyacids(vinyl
chlorideislessreactivethanethene).
GeorgeHammondformulatedausefulprinciplethatrelatesthenatureofatransitionstatetoitslocationonthereactionpath.This

HammondPostulatestatesthata
Energy
transitionstatewillbestructurally
andenergeticallysimilartothe
/\ higher
species(reactant,intermediateor
product)nearesttoitonthereaction
o begin
path.Instronglyexothermicreactions
thetransitionstatewillresemblethe
\/ lower
reactantspecies.Instronglyendothermic
conversions,suchasthatshowntothe
right,thetransitionstatewillresemblethe
highenergyintermediateorproduct,andwilltracktheenergyofthisintermediateifit
changes.Thischangeintransitionstateenergyandactivationenergyasthestabilityoftheintermediatechangesmaybeobservedby
clickingthehigherorlowerbuttonstotherightoftheenergydiagram.Threeexamplesmaybeexamined,andthereferencecurveis
changedtograyinthediagramsforhigher(magenta)andlower(green)energyintermediates.
Thecarbocationintermediateformedinthefirststepoftheadditionreactionnowassumesakeyrole,inthatitdirectlyinfluencesthe
activationenergyforthisstep.Independentresearchshowsthatthestabilityofcarbocationsvarieswiththenatureofsubstituents,ina
mannersimilartothatseenforalkylradicals.Theexceptionalstabilityofallylandbenzylcationsistheresultofchargedelocalization,and
thestabilizinginfluenceofalkylsubstituents,althoughlesspronounced,hasbeeninterpretedinasimilarfashion.
Carbocation
CH3(+) < CH3CH2(+) < (CH3)2CH(+) CH2=CHCH2(+) < C6H5CH2(+) (CH3)3C(+)
Stability
Fromthisinformation,applyingtheHammondPostulate,wearriveataplausiblerationalizationofMarkovnikov'srule.Whenan
unsymmetricallysubstituteddoublebondisprotonated,weexpectthemorestablecarbocationintermediatetobeformed
fasterthanthelessstablealternative,becausetheactivationenergyofthepathtotheformeristhelowerofthetwopossibilities.This
isillustratedbythefollowingequationfortheadditionofhydrogenchloridetopropene.Notethattheinitialacidbaseequilibriumleadsto
apicomplexwhichimmediatelyreorganizestoasigmabondedcarbocationintermediate.Themorestable2carbocationisformed
preferentially,andtheconjugatebaseoftheBrnstedacid(chlorideanionintheexampleshownbelow)thenrapidlybondstothis
electrophilicintermediatetoformthefinalproduct.

Thefollowingenergydiagramsummarizesthesefeatures.Notethatthepicomplexisnotshown,sincethisrapidlyandreversiblyformed
speciesiscommontobothpossiblereactionpaths.

AmoreextensivediscussionofthefactorsthatinfluencecarbocationstabilitymaybeaccessedbyClicking
Here.

2.RearrangementofCarbocations

2.RearrangementofCarbocations
Theformationofcarbocationsissometimesaccompaniedbyastructuralrearrangement.Suchrearrangementstakeplacebyashiftofa
neighboringalkylgrouporhydrogen,andarefavoredwhentherearrangedcarbocationismorestablethantheinitialcation.Theaddition
ofHClto3,3dimethyl1butene,forexample,leadstoanunexpectedproduct,2chloro2,3dimethylbutane,insomewhatgreateryield
than3chloro2,2dimethylbutane,theexpectedMarkovnikovproduct.Thissurprisingresultmaybeexplainedbyacarbocation
rearrangementoftheinitiallyformed2carbocationtoa3carbocationbya1,2shiftofamethylgroup.Toseethisrearrangementclick
the"ShowMechanism"buttontotherightoftheequation.

ShowMechanism

Anotherfactorthatmayinducerearrangementofcarbocationintermediatesisstrain.TheadditionofHCltopinene,themajor
hydrocarboncomponentofturpentine,givestherearrangedproduct,bornylchloride,inhighyield.Asshowninthefollowingequation,
thisrearrangementconvertsa3carbocationtoa2carbocation,atransformationthatisnormallyunfavorable.However,the
rearrangementalsoexpandsastrainedfourmemberedringtoamuchlessstrainedfivememberedring,andthisreliefofstrainprovides
adrivingforcefortherearrangement.Athreedimensionalprojectionviewoftherearrangementmaybeseenbyclickingthe"Other
View"button.Theatomnumbers(coloredred)forthepinenestructureareretainedthroughouttherearrangementtohelporientthe
viewer.Thegreennumbersinthefinalproductrepresentthepropernumberingofthisbicyclicringsystem.

OtherView

Thepropensityforstructuralrearrangementshownbycertainmolecularconstitutions,asillustratedabove,servesasausefulprobefor
theintermediacyofcarbocationsinareaction.Weshallusethistestlater.
AnextensiveandmoredetaileddiscussionofcationinducedrearrangementsmaybeaccessedbyClicking
Here.

3.AdditionofLewisAcids(ElectrophilicReagents)
Theprotonisnottheonlyelectrophilicspeciesthatinitiatesadditionreactionstothedoublebond.Lewisacidslikethehalogens,boron
hydridesandcertaintransitionmetalionsareabletobondtothealkenepielectrons,andtheresultingcomplexesrearrangeorare
attackedbynucleophilestogiveadditionproducts.Theelectrophiliccharacterofthehalogensiswellknown.Althoughfluorineis
uncontrollablyreactive,chlorine,bromineandtoalesserdegreeiodinereactselectivelywiththedoublebondofalkenes.Theadditionof
chlorineandbrominetoalkenes,asshowninthefollowinggeneralequation,proceedsbyaninitialelectrophilicattackonthepielectrons
ofthedoublebond.Iodineaddsreversiblytodoublebonds,buttheequilibriumdoesnotnormallyfavortheadditionproduct,soitisnota
usefulpreparativemethod.Dihalocompoundsinwhichthehalogensarejuxtaposedinthemannershownarecalledvicinal,fromthe
Latinvicinalis,meaningneighboring.
R2C=CR2+X2>R2CXCR2X
Otherhalogencontainingreagentswhichaddtodoublebondsincludehypohalousacids,HOX,andsulfenylchlorides,RSCl.These
reagentsareunsymmetrical,sotheiradditiontounsymmetricaldoublebondsmayinprincipletakeplaceintwoways.Inpractice,these

additionreactionsareregioselective,withoneofthetwopossibleconstitutionallyisomericproductsbeingfavored.Theelectrophilic
moietyofthesereagentsisthehalogen.
(CH3)2C=CH2+HOBr>(CH3)2COHCH2Br
(CH3)2C=CH2+C6H5SCl>(CH3)2CClCH2SC6H5
TheregioselectivityoftheabovereactionsmaybeexplainedbythesamemechanismweusedtorationalizetheMarkovnikovrule.Thus,
bondingofanelectrophilicspeciestothedoublebondofanalkeneshouldresultinpreferentialformationofthemorestable(morehighly
substituted)carbocation,andthisintermediateshouldthencombinerapidlywithanucleophilicspeciestoproducetheadditionproduct.
Thisisillustratedbythefollowingequation.

Toapplythismechanismweneedtodeterminetheelectrophilicmoietyineachofthereagents.Byusing
electronegativitydifferenceswecandissectcommonadditionreagentsintoelectrophilicandnucleophilic
moieties,asshownontheright.Inthecaseofhypochlorousandhypobromousacids(HOX),theseweak
Brnstedacids(pKa'sca.8)donotreactasprotondonorsandsinceoxygenismoreelectronegative
thanchlorineorbromine,theelectrophilewillbeahalidecation.Thenucleophilicspeciesthatbondsto
theintermediatecarbocationisthenhydroxideion,ormorelikelywater(theusualsolventforthese
reagents),andtheproductsarecalledhalohydrins.Sulfenylchloridesaddintheoppositemanner
becausetheelectrophileisasulfurcation,RS(+),whereasthenucleophilicmoietyischlorideanion
(chlorineismoreelectronegativethansulfur).
Ifyouunderstandthismechanismyoushouldbeabletowriteproductsforthefollowingreactions:

ShowProducts

Theadditionproductsformedinreactionsofalkeneswithmercuricacetateandboronhydrides(compoundsshownatthebottomofof
thereagentlist)arenormallynotisolated,butinsteadareconvertedtoalcoholsbyasubstitutionreaction.Theseimportantsynthetic
transformationsareillustratedfor2methylpropenebythefollowingequations,inwhichtheelectrophilicmoietyiscoloredredandthe
nucleophileblue.Thetopreactionsequenceillustratestheoxymercurationprocedureandthebottomisanexampleofhydroboration.

Thelightblueverticallineseparatestheadditionreactionontheleftfromthesubstitutionontheright.Theatomsorgroupsthathave
beenaddedtotheoriginaldoublebondarecoloredorangeinthefinalproduct.Inbothcasestheoverallreactionistheadditionofwater
tothedoublebond,buttheregioselectivityisreversed.TheoxymercurationreactiongivestheproductpredictedbyMarkovnikov'srule
hydroborationontheotherhandgivesthe"antiMarkovnikov"product.Complementaryreactionssuchastheseareimportantbecause
theyallowustodirectamoleculartransformationwhicheverwayisdesired.
Mercuryandboronareremovedfromtheorganicsubstrateinthesecondstepofoxymercurationandhydroborationrespectively.These
reactionsareseldomdiscussedindetailhowever,itisworthnotingthatthemercurymoietyisreducedtometallicmercuryby
borohydride(probablybywayofradicalintermediates),andboronisoxidizedtoboratebythealkalineperoxide.Additionof
hydroperoxideaniontotheelectrophilicboranegeneratesatetracoordinateboronperoxide,havingthegeneralformulaR3BOOH().
Thisundergoessuccessiveintramolecularshiftsofalkylgroupsfromborontooxygen,accompaniedineacheventbyadditionalperoxide
additiontoelectrondeficientboron.Theretentionofconfigurationofthemigratingalkylgroupisattributedtotheintramolecularnatureof
therearrangement.
Sincetheoxymercurationsequencegivesthesamehydrationproductasacidcatalyzedadditionofwater(seeBrnstedacidaddition),
wemightquestionwhythistwostepprocedureisusedatall.Thereasonliesinthemilderreactionconditionsusedforoxymercuration.
Thestrongacidusedfordirecthydrationmaynotbetoleratedbyotherfunctionalgroups,andinsomecasesmaycausemolecular
rearrangement(seeabove).
Theadditionofborane,BH3,requiresadditionalcomment.InpureformthisreagentisadimericgasB2H6,calleddiborane,butinether
orTHFsolutionitisdissociatedintoasolventcoordinatedmonomer,R2OBH3.Althoughdiboraneitselfdoesnotreacteasilywith
alkenedoublebonds,H.C.Brown(Purdue,NobelPrize1979)discoveredthatthesolvatedmonomeraddsrapidlyundermildconditions.
Boronandhydrogenhaverathersimilarelectronegativities,withhydrogenbeingslightlygreater,soitisnotlikelythereissignificant
dipolarcharactertotheBHbond.Sinceboroniselectrondeficient(itdoesnothaveavalenceshellelectronoctet)thereagentitselfisa
Lewisacidandcanbondtothepielectronsofadoublebondbydisplacementoftheethermoietyfromthesolvatedmonomer.Asshown
inthefollowingequation,thisbondingmightgenerateadipolarintermediateconsistingofanegativelychargedboronandacarbocation.
Suchaspecieswouldnotbestableandwouldrearrangetoaneutralproductbytheshiftofahydridetothecarbocationcenter.Indeed,
thishydrideshiftisbelievedtooccurconcurrentlywiththeinitialbondingtoboron,asshownbythetransitionstatedrawnbelowthe
equation,sothediscreteintermediateshownintheequationisnotactuallyformed.Nevertheless,thecarbocationstabilityrulecited
aboveremainsausefulwaytopredicttheproductsfromhydroborationreactions.Youmaycorrectthetopequationbyclickingthebutton
onitsright.Notethatthisadditionisuniqueamongthosewehavediscussed,inthatitisasinglestepprocess.Also,allthreehydrogens
inboranearepotentiallyreactive,sothatthealkylboraneproductfromthefirstadditionmayserveasthehydroborationreagentfortwo
additionalalkenemolecules.

CorrectThisEquation

ToexaminemodelsofB2H6.anditsdissociationinTHF ClickHere

StereoselectivityinAdditionReactionstoDoubleBonds
Asillustratedinthedrawingontheright,thepibondfixesthecarboncarbondoublebondinaplanarconfiguration,anddoesnotpermit
freerotationaboutthedoublebonditself.Weseethenthatadditionreactionstothisfunctionmight
occurinthreedifferentways,dependingontherelativeorientationoftheatomsorgroupsthataddto
thecarbonsofthedoublebond:(i)theymaybondfromthesameside,(ii)theymaybondfrom
oppositesides,or(iii)theymaybondrandomlyfrombothsides.Thefirsttwopossibilitiesare
examplesofstereoselectivity,thefirstbeingtermedsynaddition,andthesecondantiaddition.
Sinceinitialelectrophilicattackonthedoublebondmayoccurequallywellfromeitherside,itisinthe
secondstep(orstage)ofthereaction(bondingofthenucleophile)thatstereoselectivitymaybe
imposed.
Ifthetwostepmechanismdescribedaboveiscorrect,andifthecarbocationintermediateissufficientlylonglivedtofreelyrotateabout
thesigmabondcomponentoftheoriginaldoublebond,wewouldexpecttofindrandomornonstereoselectiveadditionintheproducts.
Ontheotherhand,iftheintermediateisshortlivedandfactorssuchassterichindranceorneighboringgroupinteractionsfavoroneside
inthesecondstep,thenstereoselectivityinproductformationislikely.Thefollowingtablesummarizestheresultsobtainedfrommany
studies,theformulaHXreferstoallthestrongBrnstedacids.Theinterestingdifferencesinstereoselectivitynotedhereprovidefurther
insightintothemechanismsoftheseadditionreactions.
Reagent

HX

X2

HOX

RSCl

Hg(OAc)2

BH3

Stereoselectivity

mixed

anti

anti

anti

anti

syn

1.BrnstedAcidAdditions
ThestereoselectivityofBrnstedacidadditionissensitivetoexperimentalconditionssuchastemperatureandreagentconcentration.
Theselectivityisoftenanti,butreportsofsynselectivityandnonselectivityarenotuncommon.Ofallthereagentsdiscussedhere,these
strongacidadditions(E=Hinthefollowingequation)comeclosesttoproceedingbytheproposedtwostepmechanisminwhicha
discretecarbocationintermediateisgeneratedinthefirststep.Suchreactionsaremostpronetorearrangementwhenthisisfavoredby
thealkenestructure.

2.AdditionReactionsInitiatedbyElectrophilicHalogen
Thehalogenschlorineandbromineaddrapidlytoawidevarietyofalkeneswithoutinducingthekindsofstructuralrearrangements
notedforstrongacids(firstexamplebelow).Thestereoselectivityoftheseadditionsisstronglyanti,asshowninmanyofthefollowing
examples.

Animportantprincipleshouldberestatedatthistime.Thealkenesshownhereareallachiral,buttheadditionproductshavechiral
centers,andinmanycasesmayexistasenantiomericstereoisomers.Intheabsenceofchiralcatalystsorreagents,reactionsofthiskind
willalwaysgiveracemicmixturesiftheproductsareenantiomeric.Ontheotherhand,iftwochiralcentersareformedintheadditionthe
reactionwillbediastereomerselective.Thisisclearlyshownbytheadditionofbrominetotheisomeric2butenes.Antiadditiontocis2
butenegivestheracemicproduct,whereasantiadditiontothetransisomergivesthemesodiastereomer.
Wecanaccountbothforthehighstereoselectivityandthelackofrearrangementinthesereactionsbyproposingastabilizinginteraction
betweenthedevelopingcarbocationcenterandtheelectronrichhalogenatomontheadjacentcarbon.Thisinteraction,whichis
depictedforbromineinthefollowingequation,delocalizesthepositivechargeontheintermediateandblockshalideionattackfromthe
synlocation.

Thestabilizationprovidedbythishalogencarbocationbondingmakesrearrangementunlikely,andinafewcasesthreememberedcyclic
haloniumcationshavebeenisolatedandidentifiedastrueintermediates.Aresonancedescriptionofsuchabromoniumionintermediate
isshownbelow.Thepositivechargeisdelocalizedoveralltheatomsofthering,butshouldbeconcentratedatthemoresubstituted
carbon(carbocationstability),andthisisthesitetowhichthenucleophilewillbond.

Thestereoselectivitydescribedhereisinlargepartduetoastereoelectroniceffect.
Thisaspectofadditionreactionsmaybeexploredbyclickinghere.
Becausetheyproceedbywayofpolarionpairintermediates,chlorineandbromineadditionreactionsarefasterinpolarsolventsthanin
nonpolarsolvents,suchashexaneorcarbontetrachloride.However,inordertopreventsolventnucleophilesfromcompetingwiththe
halideanion,thesenonpolarsolventsareoftenselectedforthesereactions.Inwateroralcoholsolutionthenucleophilicsolventmay
openthebromoniumionintermediatetogiveanhaloalcoholorether,togetherwiththeexpectedvicdihalide.Suchreactionsare
sensitivetopHandotherfactors,sowhentheseproductsaredesireditisnecessarytomodifytheadditionreagent.Aqueouschlorine
existsasthefollowingequilibrium,Keq104.ByaddingAgOH,theconcentrationofHOClcanbegreatlyincreased,andthe
chlorohydrinadditionproductobtainedfromalkenes.
Cl2+H2O

HOCl+HCl

ThemorewidelyusedHOBrreagent,hypobromousacid,iscommonlymadebyhydrolysisofNbromoacetamide,asshownbelow.Both

HOClandHOBradditionsoccurinanantifashion,andwiththeregioselectivitypredictedbythismechanism(OHbondstothemore
substitutedcarbonofthealkene).
CH3CONHBr+H2O

HOBr+CH3CONH2

Vicinalhalohydrinsprovideanalternativeroutefortheepoxidationofalkenesoverthatofreactionwithperacids.Asillustratedinthe
followingdiagram,abaseinducedintramolecularsubstitutionreactionformsathreememberedcyclicethercalledanepoxide.Boththe
halohydrinformationandhalidedisplacementreactionsarestereospecific,sostereoisomerisminthealkenewillbereflectedinthe
epoxideproduct(i.e.trans2buteneformsatransdisubstitutedepoxide).Ageneralprocedureforformingtheseusefulcompoundswill
bediscussedinthenextsection.

OtherAdditionReactions
OxidativeCleavage&DieneChemistry
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