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?

Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.

(a)

Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.

(b)

Show how to synthesize the following compounds, using appropriate carboxylic acids and amines.

(c)

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.

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

Show how you would accomplish the following syntheses. Some of these conversions may require more than one step.

(e) cyclohexylamine → N-cyclohexylacetamide

(f) bromocyclohexane → dicyclohexylmethanol