Phenol reacts with acetic anhydride in the presence of sodium acetate to produce the ester phenyl acetate:

The CH3COOi- group of phenyl acetate, like the -OH group of phenol (Practice Problem 15.8), is an ortho-para director.
(a) What structural feature of the CH3COO- group explains this?
(b) Phenyl acetate, although undergoing reaction at the ortho and para positions, is less reactive toward electrophilic aromatic substitution than phenol. Use resonance theory to explain why this is so.
(c) Aniline is often so highly reactive toward electrophilic substitution that undesirable reactions take place (see Section 15.14A). One way to avoid these undesirable reactions is to convert aniline to acetanilide (below) by treating aniline with acetyl chloride or acetic anhydride:

What kind of directive effect would you expect the acetamido group (CH3CONH-) to have?
(d) Explain why it is much less activating than the amino group, -NH2.

Transcribed Image Text:

(CH CO20 CH CO2Na он Phenol Phenyl acetate (CH CO),O NH2 Aniline Acetanilide