MCAT Organic Chemistry Practice Test 10: Nitrogen- and Phosphorus-Containing Compounds

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1. Which of the following amino acids does not have an L-enantiomer?

  • A. Cysteine
  • B. Threonine
  • C. Glutamic acid
  • D. Glycine

2. Which of the following would be formed if methyl bromide were reacted with phthalimide and followed by hydrolysis with an aqueous base?

  • A. C2H5NH2
  • B. CH3NH2
  • C. (C2H5)3N
  • D. (CH3)4N+Br–

3. Which of the following amino acids contain(s) sulfur?

I. Cysteine

II. Serine

III. Methionine

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

4. Nylon, a polyamide, is produced from hexanediamine and a substance X. This substance X is most probably a(n):

  • A. amine.
  • B. carboxylic acid.
  • C. ketone.
  • D. alcohol.

5. Intermediates in the Strecker synthesis include all of the following nitrogen-containing functional groups EXCEPT a(n):

  • A. nitrile.
  • B. imine.
  • C. amide.
  • D. amine.

6. A biochemist is synthesizing valine, shown below, using the Strecker synthesis. Which of the following carbonyl-containing compounds would be an appropriate starting reactant in this synthesis?

  • A. 2-Propanone
  • B. Propanal
  • C. 2-Methylpropanal
  • D. Butanal

7. Why is the C–N bond of an amide planar?

I. It has partial double-bond character.

II. It is sp3-hybridized.

III. It has some sp2 character.

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

8. Which of the primary methods of amino acid synthesis results in an optically active solution?

  • A. The Strecker synthesis only
  • B. The Gabriel synthesis only
  • C. Both the Strecker and Gabriel syntheses
  • D. Neither the Strecker nor the Gabriel syntheses

9. During the Gabriel synthesis, phthalimide serves as the:

  • A. nucleophile.
  • B. base.
  • C. leaving group.
  • D. electrophile.

10. Each of the following reaction types occurs during the Gabriel synthesis EXCEPT:

  • A. decarboxylation.
  • B. nucleophilic substitution.
  • C. dehydration.
  • D. hydrolysis.

11. At physiological pH, which two forms of phosphoric acid have the highest concentrations?

  • A. H3PO4 and H2PO4-
  • B. H2PO4- and HPO42-
  • C. HPO42- and PO43-
  • D. PO43- and H3PO4

12. In aqueous solution, pyrophosphate will likely:

  • A. form insoluble complexes.
  • B. be stable and inert.
  • C. degrade into inorganic phosphate.
  • D. decrease the polarity of the solvent.

13. What would be the charge of aspartic acid at pH 7?

  • A. Neutral
  • B. Negative
  • C. Positive
  • D. There is not enough information to answer the question.

14. When a bond is created between two nucleotide triphosphates in DNA synthesis, the small molecule released from this reaction is:

  • A. pyrophosphate.
  • B. inorganic phosphate.
  • C. ATP.
  • D. organic phosphate.

15. The hydrogens of phosphoric acid have pKa values that:

  • A. allow high buffering capacity over a small pH range.
  • B. allow moderate buffering capacity over a large pH range.
  • C. allow low buffering capacity over a small pH range.
  • D. do not allow buffering.