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27.03.

2015

Chemistry25b

Chemistry342M.Walker
AlternateFinalExam(3hour)
YOURNAME______________________________
360pointstotal.Youmayusemolecularmodelsforthisexam.
1.(72pointstotal)Predictthemajororganicproduct(s)foreachofthefollowingreactions.Include
thestereochemistryoftheproductwhereappropriateifracemicjustsayso.

2.(20points)Explain(usingresonanceforms)whytheHonnitrogeninsuccinimide(I)ismuchmore
acidicthanthecorrespondingHinpyrrolidine(II).

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3.(12points)Drawstructuresforanytwoofthefollowingcompounds.
a. 2bromo4nitroaniline
b. 4,4diethyl2fluorooctanal
c. (3R)cyclopropylhexanoicacid

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4.(100pointstotal)Thefollowingquestionsallrefertothereactionschemesshownbelow.Theseare
takenfromapaperonsynthesisofantiHIVdrugsina1992issueofthe"JournalofMedicinal
Chemistry".

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Chemistry25b

(a)(10points)SchemeIoutlinestwopossiblesynthesesofasecondaryamine.Whataretheproblems
associatedwithmethoda?

4(contd.).(b)(24points)Giveacompletemechanism(withcurvedarrows)forthefirstpartofrouteb
inSchemeI(thereactionoftheaminewithanarylaldehyde).

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(c)(26points)(a)WhatisthenameofthereactioninstageaofSchemeII,involvingaketone
reactingwithHCO2EtandNaOMe?Givethefullmechanism(withcurvedarrows)forthisreaction.
[Hint:Trydrawingresonanceformsoftheproducttomakeitmorefamiliar].

4(contd.).StagebinSchemeIIinvolvestheformationofaheterocyclicring,asshowninFig.1
below.Theenoltautomeroftheproductisshownastheendproduct.

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(d)(12points)IntheboxinFigure1,drawinthecurvedarrowstoshowtheelectronflowinthisstep
ofthemechanism.
(e)(10points)WhatclassofreactionisthestepfollowingtheboxedstepinFig.1?

(f)(18points)WhattypeofreactionisoccurringinthefinalstepofthemechanisminFigure1?What
isthedrivingforceforthisstep?

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Chemistry25b

5.(50points)Synthesizeanytwoofthefollowingusingthestartingmaterialsshown,andany
legitimatereagentoftwocarbonsorless.Youmayalsouseformateoracetateesters,dithianeand
phthalimide.

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Chemistry25b

6.(45points)Howmightyoueffectthefollowingtransformationsinapracticablemanner?Some
conversionsmayrequiremorethanonestep.

7.(16points)Foreachsetofthreecompounds,circlethemostacidicatthehydrogenshowninbold.

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Chemistry25b

8.(20points)Giveacompletemechanism(withcurvedarrows)forthetransesterificationreaction
shown:

9.(25points)Fillintheboxesinthefollowingsynthesiswithstructuresorreagentsasnecessary.
Includestereochemistrywhereappropriate,andindicateifracemicornot.
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GototheAlternatePracticeFinalAnswers
Gototheexampage
GototheChem342page

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