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21.E: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions (Exercises)

  • Page ID
    61704
  • These are the homework exercises to accompany the Textmap for McMurry's Organic Chemistry textbook.

    21.1 Naming Carboxylic Acid Derivatives

    21.1 Exercises

    Questions

    Q21.1.1

    Name the following compounds using IUPAC conventions

    (a)

    (b)

    (c)

    (d)

    (e)

    (f)

    (g)

    (h)

    (i)

    Solutions

    S21.1.1

    1. 3-methylpentanoyl chloride
    2. 2-cyclopentylacetamide
    3. propyl 2-methylpropanoate
    4. cyclohexylbutanoate
    5. tert-butyl cyclopentanecarboxylate
    6. 1-methylbutylcyclopentane carboxylate
    7. N-methyl-3-butenamide
    8. (S)-2-hydroxypropanoyl phosphate
    9. propyl 2,3-dimethyl-2-butenethioate

    21.3 Nucleophilic Acyl Substitution Reactions of Carboxylic Acids

    21.3 Exercises

    Questions

    Q21.3.1

    How would you create the following esters from the corresponding acids?

    (a)

    (b)

    (c)

    Q21.3.2

    The following molecule is treated with acid and undergoes an intramolecular Fischer Esterification. Draw the product.

    Solutions

    S21.3.1

    1. Acetic acid + ethanol
    2. Butanoic acid + isopropanol
    3. Cyclohexanecarboxylic acid + propanol

    S21.3.2

    21.4 Chemistry of Acid Halides

    21.4 Exercises

    Questions

    Q21.4.1

    Draw the mechanism for the following reaction

    Q21.4.2

    Propose a synthesis of the following molecules from an acid chloride and an amide.

    (a)

    (b)

    (c)

    Solutions

    S21.4.1

    S21.4.2

    1. Acetyl chloride and dimethylamine
    2. Benzoyl chloride and ethylamine
    3. Acetyl chloride and ammonia

    21.5 Chemistry of Acid Anhydrides

    21.5 Exercises

    Questions

    Q21.5.1

    Draw out the mechanism for the following reaction.

    Q21.5.2

    Draw the product of the reaction between these two molecules.

    Solutions

    S21.5.1

    S21.5.1

    21.6 Chemistry of Esters

    21.6 Exercises

    Questions

    Q21.6.1

    Why is the alkaline hydrolysis of an ester not a reversible process? Why doesn't the reaction with a hydroxide ion and a carboxylic acid produce an ester?

    Q21.6.2

    Draw the product of the reaction between the following molecule and LiAlH4, and the product of the reaction between the following molecule and DIBAL.

    Q21.6.3

    How might you Prepare the following molecules from esters and Grignards?

    (a)

    (b)

    (c)

    Solutions

    S21.6.1

    The reaction between a carboxylic acid and a hydroxide ion is an acid base reaction, which produces water and a carboxylate anion.

    S21.6.2

    21-6c.png

    S21.6.3

    (a)

    (b)

    (c)

    21.7 Chemistry of Amides

    21.7 Exercises

    Questions

    Q21.7.1

    How would you prepare the following compounds from N-Propypl benzamide?

    (a)

    (b)

    (c)

    Q21.7.2

    Propose a synthesis for the following.

    Solutions

    S21.7.1

    1. NaOH, H2O
    2. NaOH, H2O, then LAH
    3. LAH

    S21.7.2

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