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Chemistry LibreTexts

19.11: Additional Exercises

  • Page ID
    183118
  • General Review

    21-1 Provide the products for the following reactions.

    21-2 Provide the proper IUPAC name for the product of the following reaction.

    Synthesis of Carboxylic Acids

    21-3 For the following reactions, predict the final product and provide their proper IUPAC nomenclature.

    21-4 Propose another method of synthesis (starting with cyclopentane) to make the product in the previous question, 21-3.a.

    21-5 Choose the correct alkene that was oxidatively cleaved by hot, concentrated potassium permanganate to form 3-methylbutanoic acid.

    a)  (4E/Z)-oct-4-ene

    b)  (4E/Z)-2-methyloct-4-ene

    c)  (4E/Z)-2,7-dimethyloct-4-ene

    d)  (3E/Z)-2,5-dimethylhex-3-ene

     Reactions of Carboxylic Acids and Derivatives: Nucleophilic Acyl Substitution

    21-6 Provide the structures of the products of the following reactions.

    21-7 Provide the structure of the product that forms when propanoic acid reacts with thionyl chloride, then an excess of CH3CH2MgBr and finally followed by an acid workup.

    21-8 Choose the correct product of the following reaction.

    Condensation of Acids with Alcohols: the Fischer Esterification

    21-9 Predict the product of the following Fischer Esterification reaction.

    21-10 Choose the correct product of the following Fischer Esterification reaction.

    21-11 Predict the product of the following reaction (use a benzene ring with a total of two para-oriented substituents).

    Condensation of Acids with Amines: Direct Synthesis of Amides

    21-12 Give the structure of the product of the following reaction.

    21-13 Choose the correct IUPAC nomenclature of the product and provide its structure.

    a)  benzyl 4-bromohexanoate

    b)  (4E)-N-benzylhex-4-enamide

    c)  N-benzyl-4-bromohexanamide

    d)  4-bromo-N-phenylhexanamide

    21-14 Provide the structure of the final product.

    Alkylation of Carboxylic Acids to Form Ketones

    21-15 Predict the product of the following reaction.

    21-16 Explain why two equivalents of organolithium reagent is necessary to alkylate carboxylic acids (see problem 20-1).

    21-17 Give the products of the following reactions.