Name the following carboxylic acid derivatives, giving both a common name and an IUPAC name where possible.

(a) PhCOOCH₂CH(CH₃)₂

(b) PhOCHO

(c) PhCH(CH₃)COOCH₃

Name the following carboxylic acid derivatives, giving both a common name and an IUPAC name where possible.

(d) PhNHCOCH₂CH(CH₃)₂

(e) CH₃CONHCH₂Ph

Name the following carboxylic acid derivatives, giving both a common name and an IUPAC name where possible.

(f) CH₃CH(OH)CH₂CN

Name the following carboxylic acid derivatives, giving both a common name and an IUPAC name where possible.

(m)

(n)

Name the following carboxylic acid derivatives, giving both a common name and an IUPAC name where possible.

(o)

(p)

Name the following carboxylic acid derivatives, giving both a common name and an IUPAC name where possible.

(q)

(r)

Propose a mechanism for the reaction of benzyl alcohol with acetyl chloride to give benzyl acetate.

Propose a mechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride.

Propose a second mechanism for the reaction of benzoic acid with acetyl chloride to give acetic benzoic anhydride. This time, let the other oxygen of benzoic acid serve as the nucleophile to attack the carbonyl group of acetyl chloride. Because proton transfers are fast between these oxygen atoms, it is difficult to differentiate between these two mechanisms experimentally.

Propose a mechanism for the reaction of aniline with acetic anhydride to give acetanilide.

Propose a mechanism for the reaction of aniline with ethyl acetate to give acetanilide. What is the leaving group in your proposed mechanism? Would this be a suitable leaving group for an S_N2 reaction?

Which of the following proposed reactions would take place quickly under mild conditions?

(a)

(b)

(c)

(d)

(e)

Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.

(a) ethyl propionate

(b) phenyl 3-methylhexanoate

Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.

(c) benzyl benzoate

(d) cyclopropyl cyclohexanecarboxylate

Show how you would synthesize the following esters from appropriate acyl chlorides and alcohols.

(e) tert-butyl acetate

(f) diallyl succinate

Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.

(a) N,N-dimethylacetamide

(b) acetanilide (PhNHCOCH₃)

Show how you would use appropriate acyl chlorides and amines to synthesize the following amides.

(c) cyclohexanecarboxamide

(d)

Show how you would use acetic anhydride and an appropriate alcohol or amine to synthesize (i) benzyl acetate and (ii) N,N-diethylacetamide.

Propose a mechanism for the reaction of benzyl acetate with methylamine. Label the attacking nucleophile and the leaving group, and draw the transition state in which the leaving group leaves.

When ethyl 4-hydroxybutyrate is heated in the presence of a trace of a basic catalyst (sodium acetate), one of the products is a lactone. Propose a mechanism for formation of this lactone.

Acid-catalyzed transesterification:

Complete the mechanism for this acid-catalyzed transesterification by drawing out all the individual steps. Draw the important resonance contributors for each resonance-stabilized intermediate.

Propose a mechanism for the acid-catalyzed hydrolysis of phenylalanine ethyl ester.

Propose a mechanism for the following ring-opening transesterification. Use the mechanism in Problem 21-13 as a model.

1. Propose a mechanism for the acid-catalyzed reaction of salicylic acid with acetic anhydride.

2. Explain why a single drop of sulfuric acid dramatically increases the reaction rate.

Suppose we have some optically pure (R)-2-butyl acetate that has been 'labeled' with the heavy ¹⁸O isotope at one oxygen atom as shown.

(a) Draw a mechanism for the hydrolysis of this compound under basic conditions. Predict which of the products will contain the ¹⁸O label. Also predict whether the butan-2-ol product will be pure (R), pure (S), or racemized.

Suppose we have some optically pure (R)-2-butyl acetate that has been "labeled" with the heavy ¹⁸O isotope at one oxygen atom as shown.

(b) Repeat part (a) for the acid-catalyzed hydrolysis of this compound.

Suppose we have some optically pure (R)-2-butyl acetate that has been 'labeled' with the heavy ¹⁸O isotope at one oxygen atom as shown.

(c) Explain how you would prove experimentally where the ¹⁸O label appears in the products. (¹⁸O is not radioactive.)

Explain why we speak of acidic hydrolysis of an ester as acid-catalyzed, but of basic hydrolysis as base-promoted.

Soap manufacturers always use base to hydrolyze fats, and never acid. Suggest two reasons that basic hydrolysis is preferred.

Propose a mechanism for the base-promoted hydrolysis of γ-butyrolactone: