Problem Set 16_Carboxyli c Acid D erivatives CHE 311
1. Predict the product of the following reaction.
NH2
O1) LiAlH4
2 ) H2O
2. What sequence of reagents will accomplish the following transformation?
NH2
O
Cl
O
3.The ester ethyl p-nitrobenzoate is more reactive towards nucleophilic acyl substitution than
ethyl p-methyoxybenzoate. Explain this reactivity difference using both words and structures.
4. Consider the reaction below to answer the following questions:
(1) This reaction is an example of:
a. an intermolecular nucleophilic acyl substitution reaction
b. an intramolecular nucleophilic acyl substitution reaction
c. an intermolecular SN2 reaction
d. an intramolecular SN2 reaction
(2) The purpose of the base catalyst in this reaction is:
a. to polarize the carbonyl group to make it more electrophilic
b. to convert the ester to an intermediate carboxylic acid
c. to convert the alcohol group to an alkoxide anion, which is a better nucleophile
d. all of the above
(3) The product of this reaction is:
a. a lactone
b. an anhydride
c. a lactam
d. an ether
C
OEt
O
OH
NaH O
O
+ H2+ EtO-
