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    Chemistry Exam

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    Tudor Hîrlea
    This document contains a 3 hour alternate final exam for a Chemistry 342 course. It consists of 9 questions worth a total of 360 points. The questions cover a range of organic chemistry topics, including predicting products of reactions, drawing reaction mechanisms, naming reactions, proposing synthetic routes, determining relative acidities, and completing multi-step synthesis schemes. References are made to reaction schemes from a 1992 paper on anti-HIV drug synthesis. The exam instructs students to show work and includes molecular structures in some questions.

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    Chemistry Exam

    Uploaded by

    Tudor Hîrlea
    351 views10 pages
    This document contains a 3 hour alternate final exam for a Chemistry 342 course. It consists of 9 questions worth a total of 360 points. The questions cover a range of organic chemistry topics, including predicting products of reactions, drawing reaction mechanisms, naming reactions, proposing synthetic routes, determining relative acidities, and completing multi-step synthesis schemes. References are made to reaction schemes from a 1992 paper on anti-HIV drug synthesis. The exam instructs students to show work and includes molecular structures in some questions.

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    exam organic chemistry

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    Chemistry exam

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    This document contains a 3 hour alternate final exam for a Chemistry 342 course. It consists of 9 questions worth a total of 360 points. The questions cover a range of organic chemistry topics, including predicting products of reactions, drawing reaction mechanisms, naming reactions, proposing synthetic routes, determining relative acidities, and completing multi-step synthesis schemes. References are made to reaction schemes from a 1992 paper on anti-HIV drug synthesis. The exam instructs students to show work and includes molecular structures in some questions.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Flag for inappropriate content
    Download as pdf or txt
    351 views10 pages

    Chemistry Exam

    Uploaded by

    Tudor Hîrlea
    This document contains a 3 hour alternate final exam for a Chemistry 342 course. It consists of 9 questions worth a total of 360 points. The questions cover a range of organic chemistry topics, including predicting products of reactions, drawing reaction mechanisms, naming reactions, proposing synthetic routes, determining relative acidities, and completing multi-step synthesis schemes. References are made to reaction schemes from a 1992 paper on anti-HIV drug synthesis. The exam instructs students to show work and includes molecular structures in some questions.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Flag for inappropriate content
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    of 10

    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).

    http://www2.potsdam.edu/walkerma/342ts13.htm

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    Chemistry25b

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

    http://www2.potsdam.edu/walkerma/342ts13.htm

    2/10

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    Chemistry25b

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

    http://www2.potsdam.edu/walkerma/342ts13.htm

    3/10

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    Chemistry25b

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

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

    http://www2.potsdam.edu/walkerma/342ts13.htm

    4/10

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    Chemistry25b

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

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

    http://www2.potsdam.edu/walkerma/342ts13.htm

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

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

    http://www2.potsdam.edu/walkerma/342ts13.htm

    6/10

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    Chemistry25b

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

    http://www2.potsdam.edu/walkerma/342ts13.htm

    7/10

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    Chemistry25b

    6.(45points)Howmightyoueffectthefollowingtransformationsinapracticablemanner?Some
    conversionsmayrequiremorethanonestep.

    7.(16points)Foreachsetofthreecompounds,circlethemostacidicatthehydrogenshowninbold.

    http://www2.potsdam.edu/walkerma/342ts13.htm

    8/10

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    Chemistry25b

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

    9.(25points)Fillintheboxesinthefollowingsynthesiswithstructuresorreagentsasnecessary.
    Includestereochemistrywhereappropriate,andindicateifracemicornot.
    http://www2.potsdam.edu/walkerma/342ts13.htm

    9/10

    27.03.2015

    Chemistry25b

    GototheAlternatePracticeFinalAnswers
    Gototheexampage
    GototheChem342page

    http://www2.potsdam.edu/walkerma/342ts13.htm

    10/10

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