MCAT Organic Chemistry Practice Test 9: Carboxylic Acid Derivatives

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1. Which of the following would be the best method of producing methyl propanoate?

  • A. Reacting propanoic acid and methanol in the presence of a mineral acid
  • B. Reacting methanoic acid and propanol in the presence of a mineral acid
  • C. Reacting propanoic anhydride with an aqueous base
  • D. Reacting propanoic acid with an aqueous base

2. What would be the product(s) of the reaction below?

  • A.
  • B.
  • C.
  • D.

3. Which of the following undergoes a Fischer esterification most rapidly?

  • A.
  • B.
  • C.
  • D.

4. Each of the acyl compounds listed below contains a six-membered ring EXCEPT:

  • A. δ-lactam.
  • B. cyclohexane carboxylic acid.
  • C. γ-butyrolactone.
  • D. the anhydride formed from intramolecular ring closure of pentanedioic acid.

5. Which of the following would be most reactive toward nucleophiles?

  • A. Propyl ethanoate
  • B. Propanoic acid
  • C. Propanamide
  • D. Propanoic anhydride

6. How might succinic anhydride, shown below, be formed from succinic acid (butanedioic acid)?

  • A. Catalytic acid
  • B. Catalytic base
  • C. Heat
  • D. Oxidation

7. Which of the following would react most readily with a carboxylic acid to form an amide?

  • A. Methylamine
  • B. Triethylamine
  • C. Diphenylamine
  • D. Ethylmethylamine

8. If propanamide were treated with water, what product(s) would be observed?

  • A. Propanamide
  • B. Propanoic acid
  • C. Equal concentrations of propanamide and propanoic acid
  • D. Propyl propanoate

9. β-lactams are:

I. cyclic forms of the least reactive type of carboxylic acid derivative.

II. more reactive than their straight-chain counterparts.

III. molecules with high levels of ring strain.

  • A. I only
  • B. II only
  • C. II and III only
  • D. I, II, and III

10. The acid-catalyzed conversion of propyl ethanoate to benzyl ethanoate is likely:

  • A. reduction.
  • B. hydrolysis.
  • C. transesterification.
  • D. oxidation.

11. The reaction shown, which is important to breakdown of polypeptides, would be favored under what conditions?

  • A. Mild heat
  • B. Acid environment
  • C. Anhydrous environment
  • D. Nonpolar solvent

12. A positive charge on the molecule shown would have greater stability than a positive charge on a straight-chain alkane version of the same molecule. What property most explains this effect?

  • A. Steric hindrance
  • B. Nitrogen electronegativity
  • C. Induction
  • D. Conjugation

13. The molecule shown is:

I. synthesizable from a γ-hydroxycarboxylic acid.

II. a lactone.

III. a form of an ester.

  • A. I only
  • B. I and II only
  • C. II and III only
  • D. I, II, and III

14. Which reactant could be combined with butanol to form butyl acetate?

  • A. (CH3CO)2O and catalytic acid
  • B. (CH3CH2CO)2O and catalytic acid
  • C. CH3CH2CONH2 and catalytic acid
  • D. CH3CONH2 and catalytic acid

15. Why should esterification reactions NOT be carried out in water?

  • A. Carboxylic acids, from which esters are made, are generally insoluble in water.
  • B. The polar nature of water overshadows the polar nature of the leaving group.
  • C. The extensive hydrogen bonding of water interferes with the nucleophilic addition mechanism.
  • D. Water molecules would hydrolyze the desired products back into the parent carboxylic acid.