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

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

(c) cyclohexanecarboxamide

(d)

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

(a) ethyl propionate

(b) phenyl 3-methylhexanoate

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

(a)

(b)

(c)

(d)

(e)

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

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

Show how you would accomplish the following synthetic conversions efficiently and in good yield. You may use any necessary additional reagents and solvents.

(g)

Show how you would use an acid chloride as an intermediate to synthesize.

(a) N-phenylbenzamide (PhCONHPh) from benzoic acid and aniline.

Show how you would convert the following starting materials to the indicated nitriles:

(a) phenylacetic acid → phenylacetonitrile