MCAT Organic Chemistry Review

Carboxylic Acids

Practice Questions

1.    Which of these compounds would be expected to decarboxylate when heated?





2.    Carboxylic acids have higher boiling points than their corresponding alcohols primarily because:

1.    molecular weight is increased by the additional carboxyl group.

2.    the pH of the compound is lower.

3.    acid salts are soluble in water.

4.    hydrogen bonding is much stronger than in alcohols.

3.    Which of the following carboxylic acids will be the most acidic?


2.    CH3CH2CCl2COOH



4.    Which of the following molecules could be classified as a soap?

1.    CH3(CH2)17CH2COOH

2.    CH3COOH

3.    CH3(CH2)19COONa+

4.    CH3COONa+

5.    What is the final product of the following reaction?

1.    CH3(CH2)4CHO

2.    CH3(CH2)4COOH

3.    CH3(CH2)4CH3

4.    HOOC(CH2)4COOH

6.    Carboxylic acids can be reacted in one step to form all of the following compounds EXCEPT:

1.    esters.

2.    amides.

3.    alkenes.

4.    alcohols.

7.    The reduction of a carboxylic acid using lithium aluminum hydride will yield what final product?

1.    An aldehyde

2.    An ester

3.    A ketone

4.    An alcohol

8.    Which of the following is true with respect to a micelle in a hydrophilic environment?

1.    The interior is hydrophilic.

2.    The structure, as a whole, is hydrophobic.

3.    It is composed of short-chain fatty acids with polar heads.

4.    It can dissolve nonpolar molecules deep in its core.

9.    In the presence of an acid catalyst, the major product of ethanoic acid and ethanol is:

1.    acetic anhydride.

2.    butane.

3.    diethyl ether.

4.    ethyl acetate.

10.The α-hydrogen of a carboxylic acid is:

1.    more acidic than the hydroxyl hydrogen.

2.    less acidic than the hydroxyl hydrogen.

3.    very acidic, as organic compounds go.

1.    I only

2.    II only

3.    I and III only

4.    II and III only

11.The reaction of formic acid with sodium borohydride will yield what final product?

1.    An aldehyde

2.    A carboxylic acid

3.    A ketone

4.    An alcohol

12.The intramolecular reaction of 5-aminopentanoic acid through nucleophilic acyl substitution would result in a(n):

1.    anhydride.

2.    lactone.

3.    lactam.

4.    carboxylic acid.

13.Butanoic anhydride can be produced by the reaction of butanoic acid with which of the following compounds?

1.    Butanoic acid

2.    Ethanoic acid

3.    Butanol

4.    Methanal

14.Nucleophilic acyl substitution is favored by:

1.    basic solution.

2.    acidic solution.

3.    leaving groups that are strong bases.

1.    I only

2.    II only

3.    I and II only

4.    I, II, and III

15.The reaction of ammonia with caprylic acid (octanoic acid), found in coconuts, would produce a(n):

1.    ester.

2.    anhydride.

3.    alcohol.

4.    water molecule.