CHEM-2420

Problem Set 2 - Carboxylic acid and its derivatives

1. Arrange each of the following groups of compounds in order of increasing

acid strength.
a. Acetic acid, ethanol, formic acid
b. Butanoic acid, 2-chlorobutanoic acid, 3-chlorobutanoic acid
c. Sulfuric acid, 1-butyne, butanoic acid
d. 1-butyne, 1-butanol, butane

2. Heating acetic acid in an aqueous solution of oxygen-18 enriched water

(H218O) slowly forms acetic acid, in which oxygen-18 is found in the oxygen
atoms of the carbonyl group. Write a mechanism for this reaction.

3. Carry out the following syntheses using the given starting materials and any
other necessary reagents. Show all intermediate products.
O O
i OH O

ii OH N

O
iii HO
OH

O O O
iv
OC2H5 H

v O O O

OC2H5 OH
 vi O
OH
OH
Br

vii O
O
OH

vii O O
H O

ix O
Br
OH

x CH3(CH2)3C≡CH CH3(CH2)3COOCH3

4. Deduce the structures of compounds A to F.

HBr, H2O (1) NaOC2H5, C2H5OH H2, Ni D

A B C
(2) H3O+ C9H10O2
C9H10O3 C9H9BrO2

(1) Mg, dry ether

(2) CO2
O SOCl2 (3) H3O+
(1) LiAlH4 E
F

(2) H3O+