ExamName___________________________________

MULTIPLECHOICE.Choosetheonealternativethatbestcompletesthestatementoranswersthequestion. 1) TheWilliamsonethersynthesisproceedsviaan__________mechanism. A) SN1 B) SN2 C) E2 D) E1 E) noneoftheabove 2) Whatclassoforganiccompoundisthemajorproductoftheacidcatalyzedreactionofanalcohol withacarboxylicacid? A) ester B) thiol C) nitrile D) sulfonateester E) ether 3) Whichofthefollowingalcoholswillgiveapositivechromicacidtest? A) tert-butanol B) cyclohexanol C) pentan-3-ol D) bothAandB E) bothBandC 4) Identifythesequenceofreactionsthatsuccessfullycompletesthefollowingtransformation. 1)

2)

3)

4)

A) 1)BH3 2)H2 O2 /NaOH3)P,I 2 B) HI/h C) 1)HBr/h2)NaI,acetone D) AandC E) alloftheabove 5) When(R)-butan-2-olistreatedwithTsClinpyridine,theproductformedis: A) anachialcompound. B) aracemicmixture. C) asingleenantiomer. D) amixtureofdiastereomers. E) noneoftheabove. 6) WhichofthefollowingalcoholswillreactmostrapidlywiththeLucasreagent(HCl,ZnCl2 )? A) (CH3 )2 CHCH2 OH B) CH3 CH2 CH2 CH2 OH C) CH3 CH(OH)CH2 CH3 D) (CH3 )3 COH 7) WhichalcoholreactsmostrapidlywiththeLucasreagent? A) 2-propanol B) methanol C) benzylalcohol 5)

6)

7) D) isobutanol

8) Whichsetofreagentswillbestconvert2,2-dimethylpropan-1-ol(neopentylalcohol)to 4,4-dimethylpentan-2-ol? D) 1.HCl,ZnCl 2 C) 1.HCl B) 1.SOCl2 A) 1.HCl,ZnCl 2 2.Mg 2.Mg 2.Mg 2.Mg 3.CH3 CHO 3.CH2 O 3.CH3 CHO 3.CH3 CHO 4.H3 O+ + + 4.H3 O 4.H3 O 4.H3 O+ 9) Whichofthefollowingcompoundshascarboninthehighestoxidationstate? A) CH3 CH2 OH B) CO 2 C) CH3 C(OCH2 CH3 )3 D) CH3 C(O)CH3

8)

9)

10) Intheformationofthefollowingether,whichreactionispreferredandwhy?

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A) ReactionAispreferredbecausethetheformationofthecarbocationwouldbestabilizedin thebenzylicposition. B) ReactionBispreferredbecausetheoxidationstepworksbestforprimaryalcohols. C) ReactionAispreferredoverreactionBbecausethesmallermethyliodidewouldmakea betternucleophilictarget. D) ReactionBwouldbepreferredbecauseIodineisabetterleavinggroupfortheS N1reaction. E) Thereisnodifferenceinthesetworeactions-- theywouldgiveapproximatelythesame yields. SHORTANSWER.Writethewordorphrasethatbestcompleteseachstatementoranswersthequestion. 11) Providethemajororganicproductofthefollowingreaction. 11)

12) Providethemajororganicproductofthefollowingreaction.

12)

13) Withcloseattentiontostereochemistry,providethemajororganicproductforthereaction shownbelow.

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14) Providethemajororganicproductofthereactionshown.

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15) Predicttheoutcomeofthefollowingreaction.

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16) Predictthemajorproductofthereactionbelowandprovideastepwisemechanismwhich accountsforitsformation. (CH3 )3 CCH2 OH+HBr 17) Providethestructureofthemajororganicproductinthereactionbelow.

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17)

18) Providethestructureofthemajororganicproductinthereactionbelow.

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19) ShowthemostefficientuseoftheWilliamsonethersynthesistoprepare CH3 CH2 CH2 OCH(CH 3 )2.

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20) Providethestructureofthemajororganicproductinthereactionbelow. (CH3 )2 CHCH2 OH Na

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21) Providethestructureofthemajororganicproductthatresultswhen3-hexanolistreated withsodiumdichromate. 22) Providethenameofthemajororganicproductthatresultswhencyclopentanolis subjectedtothefollowingsequenceofreactions:1.TsCl,pyridine;2.LiAlH 4 . 23) Providethemajororganicproductofthereactionshown.

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22)

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24) Providethemajororganicproductofthereactionshown.

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25) Providethemajororganicproductofthefollowingreaction.

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26) Whatreagentsarenecessaryforthefollowingconversion?

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27) Providethereagentsnecessarytocarryoutthemultistepsynthesisshownbelow.

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28) Providethestructureofthemajororganicproductinthereactionbelow.

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29) Providethemajororganicproductofthereactionshown.

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30) Providethestructureofthemajororganicproductinthereactionbelow.

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31) Providethemajororganicproductofthereactionshown.

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32) Providethemajororganicproductofthereactionshown.

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33) Providethenameofthemajororganicproductthatresultswhen (R)-2-methyl-3-pentanolisheatedwithconc.H2 SO4 .. 34) Predictthemajorproductofthefollowingdehydrationreaction.

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34)

35) Providethestructureofthemajororganicproductinthereactionbelow.

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36) Providethestructureofthemajororganicproductinthereactionbelow. (CH3 )2 CHCH2 OH PBr3

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37) Providethestructureofthemajororganicproductinthereactionbelow. (CH3 )3 CCH2 CH2 OH Na2 Cr2 O7 H2 SO4

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38) Providethenameofthemajororganicproductthatresultswhencyclopentanolis subjectedtothefollowingsequenceofreactions:1.NaH;2.CH 3 CH2 Br. 39) Theenzyme,alcoholdehydrogenase,whichisproducedbytheliver,convertsethanolto __________,anormalbodymetabolite. 40) Providethemajororganicproductofthereactionshown.

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ESSAY.Writeyouranswerinthespaceprovidedoronaseparatesheetofpaper. 41) Whatseriesofsyntheticstepscouldbeusedtocarryoutthetransformationshownbelow?

42) Whatseriesofsyntheticstepscouldbeusedtocarryoutthetransformationshownbelow?

43) Whatseriesofsyntheticstepscouldbeusedtocarryoutthetransformationshownbelow?

44) WhenanalcoholisheatedinconcentratedH 2 SO4 ,dehydrationtoproducebothalkenesandethersispossible. Whichprocessismorefavoredbyhigherreactiontemperaturesandwhy? 45) Whatseriesofsyntheticstepscouldbeusedtopreparehexan-3-olfrompropan-1-ol?

46) Providethestructureofthemajororganicproductinthereactionbelow. PhCH 2 CH2 OH 1.TsC1,pyridine 2.NaCN,acetone

47) WhatseriesofsyntheticstepscouldbeusedtopreparePhCH(OH)CH 2 CH3 fromPhCH 2 OH? 48) ItisnecessarytoaddZnCl2 topromotethereactionofHClwithsomealcoholswhilethesesamealcoholsreact withHBrquitereadily.Explain. 49) Drawthestructureofdimethylsulfate,andprovideamechanismforthereactionofthiscompoundwith sodiumbenzoate(PhCO2 Na). 50) DescribethecompositionoftheJonesreagent.

AnswerKey Testname:12BALCOHOL2

1) B 2) A 3) E 4) D 5) C 6) D 7) C 8) B 9) B 10) C 11)

12)

13)

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AnswerKey Testname:12BALCOHOL2

17)

18)

19) (CH3 )2 CHO- Na++CH 3 CH2 CH2 Br 20) (CH3 )2 CHCH2 O- Na + 21) CH3 CH2 COCH 2 CH2 CH3 22) cyclopentane 23)

24)

25)

26) 1)Na 2 Cr2 O7 /H 2 SO4 2)EtOH/acidcatalyst 27) 1.H2 SO4 , 2.BH3 THF 3.H2 O2 ,NaOH 4.PCC 28) Noreaction.TertiaryalcoholsarenotoxidizedbyPCC. 29)

30)

31)

AnswerKey Testname:12BALCOHOL2

32)

33) 2-methyl-2-pentene 34)

Thisisapinacolrearrangementreactionwherethemoststablecarbocationwouldbeformedatthetertiarypositionin thering. 35)

36) (CH3 )2 CHCH2 Br 37) (CH3 )3 CCH2 CO 2 H 38) ethoxycyclopentane 39) aceticacid 40)

41) 1.Hg(OAc)2 ,CH 3 CH2 OH 2.NaBH4 or 1.BH3 2.H2 O2 , - OH 3.Na 4.CH3 CH2 I Note:ThehydrationinthesecondoptioncouldbeaccomplishedwithH + ,H2 OorHg(OAc)2 ,H2 Oaswell. 42) 1.BH3 2.H2 O2 , - OH 3.PCC 43) 1.PBr3orHBr 2.Mg,ether 3.CH3 CH2 CHO 4.H3 O+ 5.PCCorNa2 Cr2 O7 orKMnO4 44) Eliminationtoproducealkenesisfavoredbyhighertemperatures.The Sforthisprocessismorepositivethanisthe casefortheetherformation.Thisresultsinamorefavorable-TSterm,makingGfortheeliminationreactionmore negative. 10

AnswerKey Testname:12BALCOHOL2

45) 1.PCC 2.CH3 CH2 CH2 MgBr 3.H3 O+ or 1.HBrorPBr3 2.Mg,Et 2 O 3.CH3 CH2 CHO 46) PhCH 2 CH2 CN 47) 1.PCC 2.CH3 CH2 MgBr 3.H3 O+ 48) Cl- isaweakernucleophilethanisBr - .TheLewisacidZnCl 2 coordinateswiththeoxygenofthealcoholtoincrease itselectrophilicityandmakeitabetterleavinggroup. 49)

50) Jonesreagentisadilutesolutionofchromicacidinacetone.

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