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5.3: Additional Problems

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    199685

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    Exercise \(\PageIndex{1}\)

    Fill in the blanks in the following syntheses.

    clipboard_e9b1cbdc438678cc0ffe0b26a82b7b7e9.png
    Answer

    CX12BAnswer.png

    Exercise \(\PageIndex{2}\)

    Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl and nucleophilic substitution at carboxyl.

    clipboard_e39a8c030002ef77defa12a148586cfad.png
    clipboard_e2d6c9a93dd3fb9d779da9841a5f820e4.png

    Answer

    dihydrocompactinAnswer.png

    Exercise \(\PageIndex{3}\)

    Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl and nucleophilic substitution at carboxyl.

    clipboard_e9434e5965079e077da590a7ebcef6dc8.png

    Answer

    DriedBeanBeetlePheromoneAnswer.png

    Exercise \(\PageIndex{4}\)

    Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl and nucleophilic substitution at carboxyl (including Wittig and aldol reactions).

    clipboard_e04c3c690984978b5b9cf29511efdaaf4.png
    clipboard_e7331dedb4a2d2def2173584d1f20c437.png

    Answer

    CXCylindricineCAnswer.png

    Exercise \(\PageIndex{5}\)

    Fill in the blanks in the following synthesis involving nucleophilic substitution at carboxyl.

    clipboard_e8ec3a94813a11667acc3971c099ef5c4.png
    clipboard_eddba96e2e98d2eaabdd4d369b74cd4ac.png
    clipboard_e5eee2e5204270ac4c97d375b5d760dd9.png

    Answer

    ManzacidinAKawabata2013soln.png

    Exercise \(\PageIndex{6}\)

    Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl, nucleophilic substitution at carboxyl and conjugate addition.

    clipboard_ecc326c73a694ea85bf8b9d8f7eba4032.png
    clipboard_e9967a3d9396c8cac541b31da7b38a591.png
    clipboard_eaee7315847e0b68999a2798e60340560.png
    clipboard_ebab3b466f4d8167cac7aae98a849df64.png
    clipboard_e8194cc6bc970ee1d79fc008cb5a83fd9.png

    Answer

    NorzoanthamineTheodorakis2011soln.png

    Exercise \(\PageIndex{7}\)

    Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl, conjugate addition and nucleophilic substitution at carboxyl.

    clipboard_e40259be354603b010cff732c1a3e6794.png
    clipboard_e551a9075e4c49ae7965715f8378400c3.png

    Answer

    paniculatineAnswer.png

    Exercise \(\PageIndex{8}\)

    Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl, nucleophilic substitution at carboxyl and neutral nucleophilic addition to carbonyl.

    clipboard_ed6028e238aeb41e118ca1f6a1157b695.png

    Answer

    CX12CarvoneAnswer.png

    Exercise \(\PageIndex{9}\)

    Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl/em>, conjugate addition, nucleophilic substitution at carboxyl and transition metal-catalysed coupling.

    clipboard_ee85460cc41e6880c9f048a2307783359.png
    clipboard_e9cb731c7b66f04a330a26077dde9ea8f.png
    clipboard_e76758759609b8e125dfc4250afd15876.png

    Answer

    guanacastapeneanswers.png

    Exercise \(\PageIndex{10}\)

    Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl, conjugate addition, nucleophilic substitution at carboxyl and transition metal-catalysed coupling.

    clipboard_e7475da75f43336ffe0170bc8d42abf10.png

    Answer

    PhyllanthocinAnswer.png

    Exercise \(\PageIndex{11}\)

    Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl, conjugate addition, nucleophilic substitution at carboxyl, transition metal-catalysed coupling and neutral nucleophilic addition to carbonyl.

    clipboard_e9f3464926378b3f8a067f8f1b35cd746.png

    Answer

    ArtemisininAnswer.png

    Exercise \(\PageIndex{12}\)

    Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl, conjugate addition, nucleophilic substitution at carboxyl, transition metal-catalysed coupling and neutral nucleophilic addition to carbonyl.

    clipboard_e9f69f36822a7a25241d61598b645c2df.png

    Answer

    dihydrotagetoneAnswer.png

    Exercise \(\PageIndex{13}\)

    Fill in the blanks in the following synthesis involving anionic nucleophilic addition to carbonyl, conjugate addition, nucleophilic substitution at carboxyl, transition metal-catalysed coupling and neutral nucleophilic addition to carbonyl.

    clipboard_ed99576f356be467436f9acbfa389c1f7.png
    clipboard_ee2efaf160be361844c753ce395a8e2aa.png

    Answer

    sertralineAnswer.png

    Exercise \(\PageIndex{14}\)

    Fill in the blanks. Requires knowledge of formation of esters and amides as well as Wittig or Horner-Wadworth-Emmons reactions.

    clipboard_e275b93e29ba8081ee72df8a67805afd2.png
    clipboard_e3daa80b3d7ee5806e481309f14d85969.png

    Answer

    spongidepsinCossy06soln.png

    Exercise \(\PageIndex{15}\)

    In each case, analyse whether the starting material is a nucleophile or electrophile. Fill in the product in part (c). This question requires knowledge of carbonyl conjugate addition.

    These strategies are used in Fukumoto's synthesis of atisine (below).

    Answer

    atisineprequelsoln.png

    Exercise \(\PageIndex{16}\)

    Fill in the blanks in the following synthesis of atisine (Keiichiro Fukumoto, Tohoku University). Atisine is a natural product of Aconitum sp., the family of poisonous plants that includes wolfsbane.

    Requires knowledge of conjugate addition / Michael reaction, ester reductions, formation of esters and amides, and Wittig or Horner-Wadworth-Emmons reactions.

    clipboard_e5ae8c1fdc8bb48841af7ffa931e0b7b0.png
    clipboard_ed8a9d28f3749d417cf363b018660e3c6.png

    Answer

    atisineFukumoto1990soln.png

    This page titled 5.3: Additional Problems is shared under a CC BY-NC 3.0 license and was authored, remixed, and/or curated by Chris Schaller via source content that was edited to the style and standards of the LibreTexts platform; a detailed edit history is available upon request.