ACS Review Carboxylic Acids

Question 1

A mixture of 1-hexanol and hexanoic acid in diethyl ether is shaken with an aqueous sodium bicarbonate
solution. Which line below correctly describes the major organic species in the two resulting immiscible
solutions?

ether solution sodium bicarbonate solution
 A) hexanoic acid 1-hexanol 
 B) 1-hexanol hexanoic acid 
 C) sodium hexanoate 1-hexanol 
 D) 1-hexanol sodium hexanoate

Answer 1

D)

Question 2

The cleansing action of soaps is due to the formation of:
A. water insoluble micelles with lipophilic interiors
B. water soluble micelles with lipophilic interiors
C. water insoluble micelles with hydrophilic interiors
D. water soluble micelles with hydrophilic interiors

Answer 2

B.

Question 3

Which one of the following has the best soap cleansing properties?
A. CH3(CH2)16CO2H 
B. CH3CH2CO2H 
C. CH3(CH2)16CO2Na 
D. CH3CH2CO2Na

Answer 3

C.

Question 4

Which of the following is the strongest acid?

A. FCH2CO2H
B. ClCH2CO2H
C. BrCH2CO2H
D. ICH2CO2H

Answer 4

A.

Question 5

Which of the following has the largest acid equilibrium constant, Ka?
A. CH3CO2H 
B. CH2ClCO2H 
C. CHCl2CO2H 
D. CCl3CO2H

Answer 5

D.

Question 6

Rank the following three carboxylic acids in order of increasing acidity. I. 4-chlorobutanoic acid II. 3-chlorobutanoic acid III. 2-chlorobutanoic acid

A. I < II < III
B. I < III < II
C. III < I < II
D. III < II < I

Answer 6

A.

Question 7

Which of the following has the largest acid equilibrium constant, Ka?

A. benzoic acid
B. ortho-nitrobenzoic acid
C. para-methylbenzoic acid (para-toluic acid)
D. para-methoxybenzoic acid

Answer 7

B.

Question 8

What is the product of the thermal decarboxylation of dimethylpropanedioic acid? 
A. propanoic acid 
B. 2-methylpropanoic acid 
C. 2,2-dimethylpropanoic acid 
D. acetic acid

Answer 8

B.

Question 9

Chloroacetic acid, ClCH2CO2H, is a stronger acid than acetic acid. Which one of the following best
explains this?
A. ClCH2CO2¯ is more stable than CH3CO2¯ because of the electron-withdrawing Cl.
B. ClCH2CO2¯ is more soluble in water than CH3CO2¯ because of the Cl.
C. ClCH2CO2¯ is more stable than CH3CO2¯ because of an additional resonance form.
D. ClCH2CO2¯ is more stable than CH3CO2¯ because of hydrogen bonding.

Answer 9

A.