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ReactionsofAlkynes

AdditionReactionsofAlkynes
Acarboncarbontriplebondmaybelocatedatanyunbranchedsitewithinacarbonchainorattheendofachain,in
whichcaseitiscalledterminal.Becauseofitslinearconfiguration(thebondangleofasphybridizedcarbonis180
),atenmemberedcarbonringisthesmallestthatcanaccommodatethisfunctionwithoutexcessivestrain.Sincethe
mostcommonchemicaltransformationofacarboncarbondoublebondisanadditionreaction,wemightexpectthe
sametobetrueforcarboncarbontriplebonds.Indeed,mostofthealkeneadditionreactionsdiscussedearlieralso
takeplacewithalkynes,andwithsimilarregioandstereoselectivity.

1.CatalyticHydrogenation
Thecatalyticadditionofhydrogento2butynenotonlyservesasanexampleofsuchanadditionreaction,butalso
providesheatofreactiondatathatreflecttherelativethermodynamicstabilitiesofthesehydrocarbons,asshownin
thediagramtotheright.Fromtheheatsofhydrogenation,shownin
blueinunitsofkcal/mole,itwouldappearthatalkynesare
thermodynamicallylessstablethanalkenestoagreaterdegreethan
alkenesarelessstablethanalkanes.Thestandardbondenergiesfor
carboncarbonbondsconfirmthisconclusion.Thus,adoublebondis
strongerthanasinglebond,butnottwiceasstrong.Thedifference(
63kcal/mole)mayberegardedasthestrengthofthebond
component.Similarly,atriplebondisstrongerthanadoublebond,
butnot50%stronger.Herethedifference(54kcal/mole)maybe
takenasthestrengthofthesecondbond.The9kcal/mole
weakeningofthissecondbondisreflectedintheheatof
hydrogenationnumbers(36.728.3=8.4).
Sincealkynesarethermodynamicallylessstablethanalkenes,wemightexpectadditionreactionsoftheformertobe
moreexothermicandrelativelyfasterthanequivalentreactionsofthelatter.Inthecaseofcatalytichydrogenation,
theusualPtandPdhydrogenationcatalystsaresoeffectiveinpromotingadditionofhydrogentobothdoubleand
triplecarboncarbonbondsthatthealkeneintermediateformedbyhydrogenadditiontoanalkynecannotbe
isolated.Alessefficientcatalyst,Lindlar'scatalyst,preparedbydeactivating(orpoisoning)aconventional
palladiumcatalystbytreatingitwithleadacetateandquinoline,permitsalkynestobeconvertedtoalkeneswithout
furtherreductiontoanalkane.Theadditionofhydrogenisstereoselectivelysyn(e.g.2butynegivescis2butene).A
complementarystereoselectivereductionintheantimodemaybeaccomplishedbyasolutionofsodiuminliquid
ammonia.Thisreactionwillbediscussedlaterinthissection.
RCCR+H2&Lindlarcatalyst>cisRCH=CHR
RCCR+2NainNH3(liq)>transRCH=CHR+2NaNH2
Alkenesandalkynesshowacuriousdifferenceinbehaviortowardcatalytichydrogenation.Independentstudiesof
hydrogenationratesforeachclassindicatethatalkenesreactmorerapidlythanalkynes.However,careful
hydrogenationofanalkyneproceedsexclusivelytothealkeneuntiltheformerisconsumed,atwhichpointthe
productalkeneisveryrapidlyhydrogenatedtoanalkane.Thisbehaviorisnicelyexplainedbydifferencesinthe
stagesofthehydrogenationreaction.Beforehydrogencanaddtoamultiplebondthealkeneoralkynemustbe
adsorbedonthecatalystsurface.Inthisrespect,theformationofstableplatinum(andpalladium)complexeswith

alkeneshasbeendescribedearlier.Sincealkynesadsorbmorestronglytosuchcatalyticsurfacesthandoalkenes,
theypreferentiallyoccupyreactivesitesonthecatalyst.Subsequenttransferofhydrogentotheadsorbedalkyne
proceedsslowly,relativetothecorrespondinghydrogentransfertoanadsorbedalkenemolecule.Consequently,
reductionoftriplebondsoccursselectivelyatamoderaterate,followedbyrapidadditionofhydrogentothealkene
product.TheLindlarcatalystpermitsadsorptionandreductionofalkynes,butdoesnotadsorbalkenessufficientlyto
allowtheirreduction.

2.AdditionbyElectrophilicReagents
Whentheadditionreactionsofelectrophilicreagents,suchasstrongBrnstedacidsandhalogens,toalkynesare
studiedwefindacuriousparadox.Thereactionsareevenmoreexothermicthantheadditionstoalkenes,andyet
therateofadditiontoalkynesisslowerbyafactorof100to1000thanadditiontoequivalentlysubstitutedalkenes.
Thereactionofoneequivalentofbrominewith1penten4yne,forexample,gave4,5dibromo1pentyneasthe
chiefproduct.
HCCCH2CH=CH2+Br2>HCCCH2CHBrCH2Br
Althoughtheseelectrophilicadditionstoalkynesaresluggish,theydotakeplaceandgenerallydisplayMarkovnikov
Ruleregioselectivityandantistereoselectivity.Oneproblem,ofcourse,isthattheproductsoftheseadditionsare
themselvessubstitutedalkenesandcanthereforeundergofurtheraddition.Becauseoftheirhighelectronegativity,
halogensubstituentsonadoublebondacttoreduceitsnucleophilicity,andtherebydecreasetherateofelectrophilic
additionreactions.Consequently,thereisadelicatebalanceastowhethertheproductofaninitialadditiontoan
alkynewillsufferfurtheradditiontoasaturatedproduct.Althoughtheinitialalkeneproductscanoftenbeisolated
andidentified,theyarecommonlypresentinmixturesofproductsandmaynotbeobtainedinhighyield.The
followingreactionsillustratemanyofthesefeatures.Inthelastexample,1,2diodoethenedoesnotsufferfurther
additioninasmuchasvicinaldiiodoalkanesarerelativelyunstable.

Asarule,electrophilicadditionreactionstoalkenesandalkynesproceedbyinitialformationofapicomplex,in
whichtheelectrophileacceptselectronsfromandbecomesweaklybondedtothemultiplebond.Suchcomplexes
areformedreversiblyandmaythenreorganizetoareactiveintermediateinaslower,ratedeterminingstep.
Reactionswithalkynesaremoresensitivetosolventchangesandcatalyticinfluencesthanareequivalentalkenes.
Forexamplesandadiscussionofmechanismsclickhere.
Whyarethereactionsofalkyneswithelectrophilicreagentsmoresluggishthanthecorrespondingreactionsof
alkenes?Afterall,additionreactionstoalkynesaregenerallymoreexothermicthanadditionstoalkenes,andthere
wouldseemtobeahigherelectrondensityaboutthetriplebond(twobondsversusone).Twofactorsare
significantinexplainingthisapparentparadox.First,althoughtherearemoreelectronsassociatedwiththetriple
bond,thesphybridizedcarbonsexertastrongattractionfortheseelectrons,whichareconsequentlyboundmore

tightlytothefunctionalgroupthanaretheelectronsofadoublebond.Thisisseenintheionizationpotentialsof
ethyleneandacetylene.
Acetylene HCCH+Energy>[HCCH(+)+e()

H=+264kcal/mole

Ethylene

H2C=CH2+Energy>[H2C=CH2](+)+e()

H=+244kcal/mole

Ethane

H3CCH3+Energy>[H3CCH3](+)+e()

H=+296kcal/mole

Asdefinedbytheprecedingequations,anionizationpotentialistheminimumenergyrequiredtoremovean
electronfromamoleculeofacompound.Sincepielectronsarelesstightlyheldthansigmaelectrons,weexpectthe
ionizationpotentialsofethyleneandacetylenetobelowerthanthatofethane,asisthecase.Gasphaseproton
affinitiesshowthesameorder,withethylenebeingmorebasicthanacetylene,andethanebeinglessbasicthan
either.Sincetheinitialinteractionbetweenanelectrophileandanalkeneoralkyneistheformationofapicomplex,
inwhichtheelectrophileacceptselectronsfromandbecomesweaklybondedtothemultiplebond,therelatively
slowerreactionsofalkynesbecomesunderstandable.
Asecondfactorispresumedtobethestabilityofthecarbocationintermediategeneratedbysigmabondingofa
protonorotherelectrophiletooneofthetriplebondcarbonatoms.Thisintermediatehasitspositivechargelocalized
onanunsaturatedcarbon,andsuchvinylcationsarelessstablethantheirsaturatedanalogs.Indeed,wecan
modifyourearlierorderingofcarbocationstabilitytoincludethesevinylcationsinthemannershownbelow.Itis
possiblethatvinylcationsstabilizedbyconjugationwithanarylsubstituentareintermediatesinHXadditionto
alkynesofthetypeArCCR,butsuchintermediatesarenotformedinallalkyneadditionreactions.
Carbocation
CH2=CH
(+)
(+) < RCH (+) RCH=CR (+) < R CH (+)
CH
< C6H5CH2(+) R3C(+)
RCH=CH
3
2
2
Stability
CH2(+)
Methyl

1Vinyl

2Vinyl

1Allyl

1Benzyl

ApplicationoftheHammondpostulateindicatesthattheactivationenergyforthegenerationofavinylcation
intermediatewouldbehigherthanthatforalowerenergyintermediate.Thisisillustratedforalkenesversusalkynes
bythefollowingenergydiagrams.

Despitethesedifferences,electrophilicadditionstoalkyneshaveemergedasexceptionallyusefulsynthetic
transforms.Forexample,additionofHCl,aceticacidandhydrocyanicacidtoacetylenegiverespectivelytheuseful
monomersvinylchloride,vinylacetateandacrylonitrile,asshowninthefollowingequations.Notethatintheseand
manyothersimilarreactionstransitionmetals,suchascopperandmercurysalts,areeffectivecatalysts.
HCCH+HCl+HgCl2(oncarbon)>H2C=CHClvinylchloride

HCCCH2Cl+HCl+HgCl2>H2C=CClCH2Cl2,3dichloropropene
HCCH+CH3CO2H+HgSO4>H2C=CHOCOCH3vinylacetate
HCCH+HCN+Cu2Cl2>H2C=CHCNacryonitrile
Complexesformedbyalkenesandalkyneswithtransitionmetalsaredifferentfromthesimplepicomplexesnoted
above.Hereasynergicprocessinvolvingdonationofelectronsfromafilledorbitaloftheorganicligandintoan
emptydorbitalofthemetal,togetherwithbackdonationofelectronsfromanotherdorbitalofthemetalintothe
empty*antibondingorbitaloftheligand.AmodelofaPt(II)complexwithacetylenemaybeviewedbyclickinghere

3.HydrationofAlkynesandTautomerism
Aswithalkenes,theadditionofwatertoalkynesrequiresastrongacid,usuallysulfuricacid,andisfacilitatedby
mercuricsulfate.However,unliketheadditionstodoublebondswhichgivealcoholproducts,additionofwaterto
alkynesgivesketoneproducts(exceptforacetylenewhichyieldsacetaldehyde).Theexplanationforthisdeviation
liesinenolketotautomerization,illustratedbythefollowingequation.Theinitialproductfromtheadditionofwater
toanalkyneisanenol(acompoundhavingahydroxylsubstituentattachedtoadoublebond),andthisimmediately
rearrangestothemorestableketotautomer.

Tautomersaredefinedasrapidlyinterconvertedconstitutionalisomers,usuallydistinguishedbyadifferentbonding
locationforalabilehydrogenatom(coloredredhere)andadifferentlylocateddoublebond.Theequilibriumbetween
tautomersisnotonlyrapidundernormalconditions,butitoftenstronglyfavorsoneoftheisomers(acetone,for
example,is99.999%ketotautomer).Eveninsuchonesidedequilibria,evidenceforthepresenceoftheminor
tautomercomesfromthechemicalbehaviorofthecompound.Tautomericequilibriaarecatalyzedbytracesofacids
orbasesthataregenerallypresentinmostchemicalsamples.Thethreeexamplesshownbelowillustratethese
reactionsfordifferentsubstitutionsofthetriplebond.Thetautomerizationstepisindicatedbyaredarrow.For
terminalalkynestheadditionofwaterfollowstheMarkovnikovrule,asinthesecondexamplebelow,andthefinal
productiaamethylketone(exceptforacetylene,showninthefirstexample).Forinternalalkynes(thetriplebond
iswithinalongerchain)theadditionofwaterisnotregioselective.Ifthetriplebondisnotsymmetricallylocated(i.e.
ifR&R'inthethirdequationarenotthesame)twoisomericketoneswillbeformed.
HCCH+H2O+HgSO4&H2SO4>[H2C=CHOH]>H3CCH=O
RCCH+H2O+HgSO4&H2SO4>[RC(OH)=CH2]>RC(=O)CH3
RCCR'+H2O+HgSO4&H2SO4>[RHC=C(OH)R'+RC(OH)=CHR']>RCH2
C(=O)R'+RC(=O)CH2R'
Twofactorshaveanimportantinfluenceontheenolketotautomerizationsdescribedhere.Thefirstisthepotential
energydifferencebetweenthetautomericisomers.Thisfactordeterminesthepositionoftheequilibriumstate.The
secondfactoristheactivationenergyfortheinterconversionofonetautomertotheother.Thisfactordeterminesthe
rateofrearrangement.Sincethepotentialenergyorstabilityofacompoundisinlargepartafunctionofitscovalent
bondenergies,wecanestimatetherelativeenergyofketoandenoltautomersbyconsideringthebondsthatare
changedintherearrangement.Fromthefollowingdiagram,weseethatonlythreesignificantchangesoccur,and
thestandardbondenergiesforthosechangesaregiventotherightoftheequation.Theketotautomerhasa17.5
kcal/moleadvantageinbondenergy,soitspredominanceatequilibriumisexpected.

Therapiditywithwhichenolketotautomerizationoccurssuggeststhattheactivationenergyforthisprocessislow.
Wehavenotedthattherearrangementisacid&basecatalyzed,andverycarefulexperimentshaveshownthat
interconversionoftautomersismuchslowerifsuchcatalystsareabsent.Astrikingexampleoftheinfluenceof
activationenergyonsuchtransformationsmaybeseeninthefollowinghypotheticalrearrangement.Herewehave
substitutedamethylgroup(coloredmaroon)fortheprotonofaconventionaltautomerism,andthemethylshiftsfrom
oxygentocarbonjustastheprotondoesingoingfromanenoltoaketone.
H2C=CHOCH3X>CH3CH2CH=O
Thepotentialenergychangeforthisrearrangementisevenmoreadvantageousthanforenolketotautomerism,
beingestimatedatover25kcal/molefrombondenergychanges.Despitethisthermodynamicdrivingforce,theenol
etherdescribedaboveiscompletelystabletobasetreatment,andundergoesrapidacidcatalyzedhydrolysiswith
lossofmethanol,ratherthanrearrangement.Thecontrollingdifferenceinthiscasemustbeaprohibitivelyhigh
activationenergyforthedescribedrearrangement,combinedwithlowerenergyalternativereactionpaths.

4.HydroborationReactions
Diboranereactsreadilywithalkynes,buttheformationofsubstitutedalkeneproductsleavesopenthepossibilityofa
secondadditionreaction.Aclevertechniqueforavoidingthiseventtakesadvantageofthefactthatalkynesdonot
generallysufferfromsterichindrancenearthetriplebond(theconfigurationofthisfunctionalgroupislinear).
Consequently,largeorbulkyelectrophilicreagentsaddeasilytothetriplebond,buttheresultingalkeneis
necessarilymorecrowdedorstericallyhinderedandresistsfurtheradditions.Thebulkyhydroborationreagent
neededforthisstrategyispreparedbyreactionofdiboranewith2methyl2butene,ahighlybranchedalkene.
Becauseofthealkylbranching,onlytwoalkenesaddtoaBH3moiety(sterichindranceagain),leavingoneBH
covalentbondavailableforreactionwithanalkyne,asshownbelow.Theresultingdialkylboraneiscalled
disiamylborane,acontractionofdisecondaryisoamylborane(amylisanoldnameforpentyl).
2(CH3)2C=CHCH3+BH3inether>[(CH3)2CHCH(CH3)]2BHdisiamylborane
Animportantapplicationofdisiamylboraneisitsadditionreactiontoterminalalkynes.Aswithalkenes,theBH
reagentgroupaddsinanapparentlyantiMarkovnikovmanner,duetothefactthattheboronistheelectrophile,not
thehydrogen.Furtheradditiontotheresultingboronsubstitutedalkenedoesnotoccur,andtheusualoxidative
removalofboronbyalkalinehydrogenperoxidegivesanenolwhichrapidlyrearrangestothealdehydetautomer.
Thus,bytheproperchoiceofreagents,terminalalkynesmaybeconvertedeithertomethylketones(mercuricion
catalyzedhydration)oraldehydes(hydroborationfollowedbyoxidation).
RCCH+(C5H11)2BH>[RCH=CHB(C5H11)2]+H2O2&NaOH>[RCH=CHOH]

>RCH2CH=O
Hydroborationofinternalalkynesisnotaparticularlyusefulprocedurebecauseamixtureofproductswilloftenbe
obtained,unlessthetriplebondissymmetricallysubstituted.Mercuricioncatalyzedhydrationgivessimilarresults.

5.Oxidations

5.Oxidations
Reactionsofalkyneswithoxidizingagentssuchaspotassiumpermanganateandozoneusuallyresultincleavageof
thetriplebondtogivecarboxylicacidproducts.Ageneralequationforthiskindoftransformationfollows.Thesymbol
[O]isoftenusedinageneralwaytodenoteanoxidation.
RCCR'+[O]>RCO2H+R'CO2H

NucleophilicAdditionReactions&Reduction
NucleophilicAdditionReactions&Reduction
Thesphybridcarbonatomsofthetriplebondrenderalkynesmoreelectrophilicthansimilarlysubstitutedalkenes.
Asaresult,alkynessometimesundergoadditionreactionsinitiatedbybondingtoanucleophile.Thismodeof
reaction,illustratedbelow,isgenerallynotdisplayedbyalkenes,unlessthedoublebondisactivatedby
electronegativesubstituents,e.g.F2C=CF2,orbyconjugationwithanelectronwithdrawinggroup.
HCCH+KOC2H5inC2H5OHat150C>H2C=CHOC2H5
HCCH+HCN+NaCN(catalytic)>H2C=CHCN
Thesmallestandmostreactivenucleophilicspeciesisprobablyanelectron.Electronadditiontoafunctionalgroupis
bydefinitionareduction,andwenotedearlierthatalkynesarereducedbysolutionsofsodiuminliquidammoniato
transalkenes.Tounderstandhowthisreductionoccurswefirstneedtoidentifytwodistinctreactionsofsodiumwith
liquidammonia(boilingpoint78C).Inthefirst,sodiumdissolvesinthepureliquidtogiveadeepbluesolution
consistingofverymobileandlooselyboundelectronstogetherwithsolvatedsodiumcations(firstequationbelow).
Forpracticalpurposes,wecanconsidersuchsolutionstobeasourceof"freeelectrons"whichmaybeusedas
powerfulreducingagents.Inthesecondcase,ferricsaltscatalyzethereactionofsodiumwithammonia,liberating
hydrogenandformingthecolorlesssaltsodiumamide(secondequation).Thisisanalogoustothereactionofsodium
withwatertogivesodiumhydroxide,butsinceammoniais1018timesweakeranacidthanwater,thereactionisless
violent.Theusefulnessofthisreactionisthatsodiumamide,NaNH2,isanexceedinglystrongbase(18powersof
tenstrongerthansodiumhydroxide),whichmaybeusedtoconvertveryweakacidsintotheirconjugatebases.
Na+NH3(liquid,78C)>Na(+)+e()(abluesolution)
Na+NH3(liquid,78C)+Fe>H2+NaNH2(acolorlesssolution)
Returningtothereducingcapabilityoftheblueelectronsolutions,wecanwriteaplausiblemechanismforthe
reductionofalkynestotransalkenes,asshownbelow.Isolatedcarbondoublebondsarenotreducedbysodiumin
liquidammonia,confirmingtheelectronegativitydifferencebetweenspandsp2hybridizedcarbons.

AcidityofTerminalAlkynes
AcidityofTerminalAlkynes
AlkanesareundoubtedlytheweakestBrnstedacidscommonlyencounteredinorganicchemistry.Itisdifficultto
measuresuchweakacids,butestimatesputthepKaofethaneatabout48.Hybridizingthecarbonsoastoincrease
thescharacteroftheCHincreasestheacidity,withthegreatestchangeoccurringforthespCHgroupsfoundin
terminalalkynes.Thus,thepKaofetheneisestimatedat44,andthepKaofethyne(acetylene)isfoundtobe25,
makingit1023timesstrongeranacidthanethane.Thisincreaseinaciditypermitstheisolationofinsolublesilverand
coppersaltsofsuchcompounds.
RCCH+Ag(NH3)2(+)(inNH4OH)>RCCAg(insoluble)+NH3+NH4(+)
Despitethedramaticincreaseinacidityofterminalalkynesrelativetootherhydrocarbons,theyarestillveryweak
acids,especiallywhencomparedwithwater,whichisroughlyabilliontimesmoreacidic.Ifwewishtoprepare
nucleophilicsaltsofterminalalkynesforuseinsynthesis,itwillthereforebenecessarytouseamuchstrongerbase
thanhydroxide(orethoxide)anion.Suchabaseissodiumamide(NaNH2),discussedabove,anditsreactionswith
terminalalkynesmaybeconductedinliquidammoniaoretherassolvents.Theproductsofthisacidbasereaction
areammoniaandasodiumacetylidesalt.Becausetheacetylideanionisapowerfulnucleophileitmaydisplace
halideionsfrom1alkylhalidestogiveamorehighlysubstitutedalkyneasaproduct(SN2reaction).Thissynthesis
applicationisdescribedinthefollowingequations.Thefirsttwoequationsshowhowacetylenecanbeconvertedto
propynethelasttwoequationspresentasynthesisof2pentynefrompropyne.
HCCH+NaNH2(inammoniaorether)>HCCNa(sodiumacetylide)+NH3
HCCNa+CH3I>HCCCH3+NaI
CH3CCH+NaNH2(inammoniaorether)>CH3CCNa(sodiumpropynylide)+NH3
CH3CCNa+C2H5Br>CH3CCC2H5+NaBr
BecauseRCC:()Na(+)isaverystrongbase(roughlyabilliontimesstrongerthanNaOH),itsuseasanucleophile
inSN2reactionsislimitedto1alkylhalides2and3alkylhalidesundergoeliminationbyanE2mechanism.
Theenhancedacidityofterminalalkynesrelativetoalkanesalsoleadstometalexchangereactionswhenthese

compoundsaretreatedwithorganolithiumorGrignardreagents.Thisexchange,shownbelowinequation1,canbe
interpretedasanacidbasereactionwhich,asexpected,proceedsinthedirectionoftheweakeracidandthe
weakerbase.ThisfactorclearlylimitstheusefulnessofGrignardorlithiumreagentswhenaterminaltriplebondis
present,asinequation2.
1)RCCH+C2H5MgBr(inether)>RCCMgBr+C2H6
2)HCCCH2CH2Br+Mg(inether)>[HCCCH2CH2MgBr]>BrMgCCCH2CH2H
Theacidityofterminalalkynesalsoplaysaroleinproductdeterminationwhenvicinal(orgeminal)dihalidesundergo
baseinducedbiseliminationreactions.Thefollowingexampleillustrateseliminationsofthiskindstartingfrom1,2
dibromopentane,preparedfrom1pentenebyadditionofbromine.Theinitialeliminationpresumablyforms1bromo
1pentene,sincebaseattackatthemoreacidicandlesshindered1carbonshouldbefavored.Thesecond
eliminationthenproduces1pentyne.Iftheverystrongbasesodiumamideisused,theterminalalkyneistrappedas
itssodiumsalt,fromwhichitmaybereleasedbymildacidtreatment.However,iftheweakerbaseKOHisusedfor
theelimination,theterminalalkynesaltisnotformed,orisformedreversibly,andtheinitiallygenerated1pentyne
rearrangestothemorestable2pentyneviaanalleneintermediate.

Inthecaseofnonterminalalkynes,sodiumandpotassiumamide,andrelatedstrongbasesfrom1amines,are
abletoabstractprotonsfromcarbonatomsadjacenttothetriplebond.Theresultingalleniccarbanionsundergo
rapidprotontransferequilibria,leadingtotherelativelystableterminalalkyneconjugatebase.Thisisomerizationmay
beusedtopreparelongerchain1alkynes,asshowninthefollowingconversionof3heptyneto1heptyne.TheR
andR'substituentsontheallenicintermediaterangefrompropyltohydrogen,astheprotontransfersproceed.

PracticeProblems
Thefollowingproblemsreviewthechemistryofalkynes.Thefirstquestionrequiresyoutoselectoneoftwo

startingalkynesandoneofninepossiblereagentsystemstoprepareadesignatedproduct.Thesecond
questionasksyoutodrawtheproductsfromvariousalkyne+reagentcombinations.
ChooseaProblem

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