9.3 Nucleophilic Acyl Substitution Reactions

Question 1

nucleophilic acyl substitution reaction

Answer 1

a nucleophile forms a new bond with the carbonyl carbon of an acyl group with accompanying breakage of a bond between the carbonyl carbon and a leaving group

Question 2

acyl

Answer 2

Question 3

anhydride cleavage: ammonia nucleophile

Answer 3

anhydrides can undergo a nucleophilic substitution reaction with ammonia as the nucleophile and a carboxyl as a leaving group

results in an amide and a carboxylic acid

Question 4

anhydride cleavage: alcohol nucleophile

Answer 4

anhydrides can undergo a nucleophilic substitution reaction with alcohol as the nucleophile and carboxyl group as the leaving group

results in an ester and carboxylic acid

Question 5

anhydride cleavage: water nucleophile

Answer 5

anhydrides can undergo a nucleophilic substitution reaction with water as the nucleophile and a carboxyl as the leaving group

results in 2 carboxylic acids

Question 6

transesterification

Answer 6

an alcohol acts as nucleophiles to replace the esterifying group on an ester

one ester is simply transformed to another

Question 7

hydrolysis of amides

Answer 7

amides can undergo a nucleophilic substitution reaction with water as the nucleophile and ammonia as the leaving group

results in ammonia and carboxylic acid

strong acid or base is needed to catalyze this reaction