22. Carboxylic Acid Derivatives: NAS

Write the mechanism for each of the following reactions:

b. the reaction of benzoyl chloride with excess methylamine to form N-methylbenzamide

What compounds are formed from the reaction of benzoyl chloride with the following reagents?

a. sodium acetate

b. water

Identify the major and minor products of the following reaction:

An aqueous solution of a primary or secondary amine reacts with an acyl chloride to form an amide as the major product. However, if the amine is ­tertiary, an amide is not formed. What product is formed? Explain.

a. Identify the two products obtained from the following reaction:

What reagent should be used to carry out the following reaction?

What are the products of the following reactions?

a.

b.

Give the products expected from the following reactions.

(a) acetyl chloride + ethylamine

(b)

(c)

Draw the product of each of the following reactions:

b.

What are the products of the following reactions?

a.

Propose mechanisms for the nucleophilic acyl substitutions to form N-methylacetamide as shown on the previous page.

Propose mechanisms for the nucleophilic acyl substitutions to form ethyl benzoate as shown on the previous page.

Predict the products and propose mechanisms for the following reactions.

(d)

Predict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.

(a) ethanol

(b) sodium acetate

(c) aniline

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

(c) cyclohexanecarboxamide

(d)