22. Carboxylic Acid Derivatives: NAS

What products would you expect to obtain from the following reactions?

c. urea + water

d. β-ethylglutaric acid + acetyl chloride + Δ

Which ester hydrolyzes more rapidly? a. methyl acetate or phenyl acetate?

Which ester hydrolyzes more rapidly? b. phenyl acetate or benzyl acetate?

Compare each of the mechanisms listed here with the mechanism for each of the two parts of the acid-catalyzed hydrolysis of an ester, indicating a. similarities. b. differences.

1. acid-catalyzed formation of a hydrate

For each heterocyclic compound,

(ii) show what compounds would result from complete hydrolysis.

(a)

(b)

(c)

How could you convert N-methylbenzamide to the following compounds?

b. benzoic acid

How could you convert N-methylbenzamide to the following compounds?

d. benzyl alcohol

Which alkyl halides form the carboxylic acids listed here after reaction with sodium cyanide followed by heating the product in an acidic aqueous solution?

a. butyric acid

b. isovaleric acid

Because bromocyclohexane is a secondary alkyl halide, both cyclohexanol and cyclohexene are formed when the alkyl halide reacts with hydroxide ion. Suggest a method to synthesize cyclohexanol from bromocyclohexane that forms little or no cyclohexene.

What reagents would you use to convert methyl propanoate to the following compounds?

c. N-ethylpropanamide

d. propanoic acid

Describe how the target molecule (butanone) can be synthesized in a high yield from butane.

Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.

a.

Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.

b.

Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.

d.

How would you make the following compounds from N-benzylbenzamide?

b. benzoic acid