22. Carboxylic Acid Derivatives: NAS

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

(d) ethyl acetate → 3-methylpentan-3-ol

Diazomethane can be used to convert a carboxylic acid to a methyl ester. Propose a mechanism for this reaction.

The reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, does not work with primary alcohols.

a. Propose a mechanism for the Ritter reaction.

What is the product of an acyl substitution reaction—a new carboxylic acid derivative, a mixture of two ­carboxylic acid derivatives, or no reaction—if the new group in the tetrahedral intermediate is the following? b. a weaker base than the substituent that is attached to the acyl group

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

g. excess benzylamine

h. 4-chlorophenol

Propose a mechanism for each of the following reactions:

b.

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

a.

Propose a mechanism for the reaction of benzyl acetate with methylamine. Label the attacking nucleophile and the leaving group, and draw the transition state in which the leaving group leaves.

Write the mechanism for each of the following reactions:

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

Write the mechanism for the reaction of an amino acid with di-tert-butyl dicarbonate.

Propose a mechanism for the formation of succinic anhydride from succinic acid in the presence of acetic anhydride at neutral pH.

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

(a) ethanol

(b) sodium acetate

(c) aniline

Determine the major product for the following reaction.

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

(c) isobutylamine → N-isobutylformamide