CHEM210 [ CHAPTER 10 ADDITIONAL BOOK PROBLEMS]

PROBLEMSGRAYEDOUTWERENOTCOVEREDINCLASSNONEEDTOCOMPLETE

1.GivetheIUPACnameforthefollowingcompound.

A)(Z)2,3,6trimethyl2heptene
B)(Z)2,3,6trimethyl3heptene
C)(E)2,3,6trimethyl3heptene
D)(E)2,3,6trimethyl2heptene
E)(E)2,4,6trimethyl3heptene

2.GivetheIUPACnameforthefollowingcompound.

A)(E)4ethyl3octene
B)(Z)4ethyl3nonene
C)(E)3ethyl4nonene
D)(E)4ethyl3nonene
E)(E)5ethyl6nonene

3.GivetheIUPACnameforthefollowingcompound.

A)(Z)1bromo2chloro2ethyl4methyl1pentene
B)(E)1bromo1chloro2ethyl4methyl2pentene
C)(E)1bromo1chloro2ethyl4methyl1pentene
D)(E)1bromo1chloro3ethyl4methyl1pentene
E)(Z)1bromo1chloro2ethyl4methyl1pentene

4.GivetheIUPACnameforthefollowingcompound.

A)(E)4ethyl2,5dimethyl3octene
B)(Z)4ethyl2,5dimethyl3octene
C)(E)5ethyl6,3dimethyl6octene
D)(E)4ethyl2,5dimethyl4octene
E)(E)2ethyl4,5dimethyl3octene

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5.Whichofthefollowingstatementsis(are)trueaboutcompoundA?

A)Aisatransalkene.
B)AisanEalkene.
C)Aisacisalkene.
D)Both(Aisatransalkene)and(AisanEalkene)aretrue.
E)Both(AisanEalkene)and(Aisacisalkene)aretrue.

6.Determinethestereochemistryofthefollowingalkenes.

A)a:Z;b:Z;c:E;d:E
B)a:Z;b:Z;c:Z;d:E
C)a:E;b:Z;c:E;d:E
D)a:Z;b:E;c:E;d:E
E)a:Z;b:Z;c:E;d:Z

7.Whichofthefollowingcompoundshasthehighestboilingpoint?

8.Whichofthefollowingcompoundshasthehighestboilingpoint?

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9.Rankthefollowingcompoundsfromleasttomoststable.

A)a,b,cD)b,a,c
B)b,c,aE)c,b,a
C)c,a,b

10.Rankthefollowingcompoundsfromleasttomoststable.

A)a,b,cC)c,a,b
B)b,c,aD)b,a,c

11.WhichofthefollowingreactionsisanexampleofMarkovnikov'srule?

12.WhichofthefollowingreactionconditionswouldresultinantiMarkovnikovadditiontoanalkene?
A)H2O/H+
B)HBr
C)HCl
D)[1]BH3;[2]H2O2/OH

13.WhichofthefollowingalkeneswillreactfastestwithwaterinthepresenceofasmallamountofH2SO4?

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14.Inwhichofthefollowingalkeneadditionreactionswillcarbocationrearrangementsoccur?
A)TheadditionofBr2andH2O;halohydrinformation
B)TheadditionofBr2
C)TheadditionofH2Ointhepresenceofacid
D)Reactions(TheadditionofBr2andH2O;halohydrinformation)and(TheadditionofH2Ointhepresenceofacid)
willbothshowcarbocationrearrangements.
E)Reactions(TheadditionofBr2andH2O;halohydrinformation),(TheadditionofBr2),and(TheadditionofH2O
inthepresenceofacid)willallshowcarbocationrearrangements.

15.MarkovnikovadditionofHBrtoCH3CH
CH2involves:
A)initialattackbyBr.
B)initialattackbyBr.
C)isomerizationofCH3CH2CH2Br.
D)formationofaprimarycarbocation.
E)formationofasecondarycarbocation.

16.Rearrangementscanoccurinwhichofthefollowingreactions?
A)AcidcatalyzedadditionofH2Otoanalkene.
B)E2elimination.
C)Freeradicalhalogenationofalkanes.
D)AdditionofCl2toanalkene.
E)Noneofthechoicesiscorrect.

17.WhichofthefollowingalkenesreactsfastestwithHCl?

18.Inwhichofthefollowingreactionscanrearrangementsoccur?
A)AcidcatalyzedadditionofH2Otoanalkene
B)Acidcatalyzeddehydrationofanalcoholtoformanalkene
C)TheadditionofHBrtoanalkene
D)Rearrangementsoccuronlyinreactions(Acidcatalyzeddehydrationofanalcoholtoformanalkene)and(The
additionofHBrtoanalkene).
E)Rearrangementsoccurinreactions(AcidcatalyzedadditionofH2Otoanalkene),(Acidcatalyzeddehydrationof
analcoholtoformanalkene),and(TheadditionofHBrtoanalkene).

19.AcompoundMwithmolecularformulaC8H12andnotriplebondsreactswithH2togiveanewcompoundhaving
molecularformulaC8H14.WhatcanbesaidaboutM?
A)Mhas3rings.
B)Mhas2ringsand1bond.
C)Mhas1ringand2bonds.
D)Mhas3bonds.
E)It'simpossibletosayanythingaboutthestructureofMgiventhisdata.

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20.WhichcompoundismostreactivetowardsHBr?

21.Predictthemajorproductofthefollowingreaction.

22.Predicttheproduct(s)ofthefollowingreaction.

23.Predicttheproductofthefollowingreaction.

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24.Predicttheproduct(s)ofthefollowingreaction.

25.Predicttheproduct(s)ofthefollowingreaction.

26.Predicttheproduct(s)ofthefollowingreaction.

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27.Whichisnotastereoisomerofthecompoundbelow?

28.Predicttheproductofthefollowingreaction.

29.Predicttheproduct(s)ofthefollowingreaction.

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30.Predicttheproduct(s)ofthefollowingreaction.

31.Considerthereactionbelowanddeterminewhichofthefollowingstatementsistrue.

A)TheprimaryalcoholisformedsincethistypeofreactionalwaysleadstotheMarkovnikovproduct.
B)ThesecondaryalcoholisformedsincethistypeofreactionalwaysleadstotheMarkovnikovproduct.
C)TheprimaryalcoholisformedsincethistypeofreactionalwaysleadstotheantiMarkovnikovproduct.
D)ThesecondaryalcoholisformedsincethistypeofreactionalwaysleadstotheantiMarkovnikovproduct.
E)Amixtureofprimary,secondaryandtertiaryalcoholsproductsareformed.

32.Predicttheproduct(s)ofthefollowingreaction.

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33.Predicttheproduct(s)ofthefollowingreaction.

A)AD)BandC
B)BE)A,B,CandD
C)AandD

34.Whichisnotaproductofthisreaction?

35.Predicttheproductofthefollowingreaction.

A)AD)BandC
B)BE)A,B,CandD
C)AandD

36.Whichofthefollowingcouldbeusedtopreparethefollowingalkylhalide?

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37.Theonlypossiblestartingmaterialforthereactionbelowis2methylpropene.

A)TrueB)False

38.Whatisthestartingmaterialinthereactionbelow?

39.Whatis(are)themissingreagent(s)inthereactionbelow?

A)Br2/CCl4
B)[1]BH3,[2]H2O2/OH
C)9BBN
D)NBS
E)[1]Br2,[2]H2O

40.Whatis(are)themissingreagent(s)inthereactionbelow?

A)Br2/CCl4
B)[1]BH3,[2]H2O2/OH
C)9BBN
D)NBS
E)[1]Br2,[2]H2O

41.Fromthelistofpossiblecarbocations,whichonewouldnotbelikelytorearrange?

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42.Eachofthefollowingcompoundswillbesubjectedtocompletecombustion.Ifonemoleofeachcompoundisused,
whichonewillliberatethemostheat?
A)1pentene
B)2pentene
C)3methyl1butene
D)2methyl1butene
E)2methyl2butene

43.Youaretosynthesize1butenefrom2bromobutane.Youmustgetthehighestyieldpossible.Fromthelistof
reagentsgivenbelow,whichonewouldyouusetoobtainthegreatestyield?
A)AlcoholicKOH
B)KOHandwater
C)tButylalcoholand(CH3CH2)3COK
D)EthanolandCH3CH2ONa
E)MethanolandCH3ONa

44.WhatistheinitialmechanisticstepfortheadditionofHCltopropene?
A)initialattackbyachlorideion
B)initialattackbyachlorineatom
C)isomerizationof1chloropropane
D)formationofa1carbocation
E)formationofa2carbocation

45.Whichreactionofanalkeneproceedsexclusivelywithantiaddition?
A)Hydroboration/oxidation
B)Bromination
C)Permanganateoxidation
D)Hydrogenation
E)HBraddition

46.ForwhichofthefollowingalkenesisEZisomerismpossible?
A.CH3CH2CH=CHCH2CH3
B.CH3CH2CH=CHBr
C.(CH3)2C=CHCH3

D.H2C=CHCH2CH(CH3)2

A)AandBD)A,B,C
B)AandCE)A,B,C,andD
C)BandD

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ChallengeQuestions

47.ProvideanIUPACnameforthefollowingcompound.

A)(E)10Chloro2methyl9decen1,7diol
B)(Z)1Chloro9methyl1decen4,10diol
C)(E)1Chloro9methyl1decen4,10diol
D)(Z)10Chloro2methyl9decen1,7diol

48.Dienesundergomanyofthesametypesofreactionsasalkenes.ConsiderthemechanismforaMarkovnikov
additionofHBrtothefollowingdieneandpredictthemajorproduct.

49.()CallystatinA(1)wasisolatedin1997fromthemarinespongeCallyspongiatruncataandexhibitspotent
cytotoxicity.DeterminethestereochemistryoftheselectedC=Cbondsandstereocenters.

A)(a)=Z,(b)=R,(c)=E,(d)=R
B)(a)=E,(b)=S,(c)=Z,(d)=S
C)(a)=Z,(b)=S,(c)=E,(d)=R
D)(a)=Z,(b)=R,(c)=E,(d)=S
E)(a)=E,(b)=R,(c)=Z,(d)=R

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50.Thereactionbelowisoneofthestepsusedinthesynthesisof(+/)PerhydrohistrionicotoxinbyCooteandco
workers.Predictwhichofthefollowingsetsofreagentscouldbeusedforthistransformation.

51.Determinethestructureofthefinalproductwhen3careneissubjectedtothefollowingreactionconditions.

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AnswerKeyChapter10:Alkenes
1.
2
3.
4.
5.
6.
7.
8.
9.
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11.
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13.
14.
15.
16.
17.
18.
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20.
21.
22.
23
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51.

C
D
E
A
D
C
B
C
D
C
B
D
E
C
E
A
D
E
B
B
A
E
C
F
E
F
C
B
F
B,C
C
D
D
B
D
A
A
B
B
A
C
E
C
E
B
A
D
E
A
C
C

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