20.14: Solutions to Additional Exercises

General Review

22-1

Possible set of reactants:

22-2

22-3

22-4

Interconversion of Acid Derivatives by Nucleophilic Acyl Substitution

22-5:

22-6:

22-7:

Answer: B

Transesterification

22-8:

Answer: D

22-9:

Under acidic conditions, the carbonyl oxygen atom is protonated, making it a better electrophile for the reaction to occur. Under basic conditions, the alcohol we are trying to add is deprotonated, making it a better nucleophile.

22-10:

Hydrolysis of Carboxylic Acid Derivatives

22-11:

22-12:

22-13:

Reduction of Acid Derivatives

22-14:

22-15:

22-16:

Answer: C

Reactions of Acid Derivatives with Organometallic Reagents

22-17:

22-18:

Answer: C

22-19:

A possibly better route of synthesis: