MCAT Organic Chemistry Practice Test 4: Analyzing Organic Reactions

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1. Which of the following are Lewis bases?

I. Ag+

II. H2O

III. NH3

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

2. Rank the following in order of decreasing nucleophilicity in an aprotic solvent: RO–, RCOOH, ROH, HO–

  • A. RCOOH > ROH > RO– > HO–
  • B. HO– > ROH > RO– > RCOOH
  • C. RO– > HO– > ROH > RCOOH
  • D. RCOOH > RO– > HO– > ROH

3. Rank the following in order of decreasing electrophilicity: CR3+, CH3OH, CH3OCH3, CH3Cl

  • A. CH3OCH3 > CR3+ > CH3OH > CH3Cl
  • B. CR3+ > CH3OH > CH3OCH3 > CH3Cl
  • C. CH3OCH3 > CH3Cl > CR3+ > CH3OH
  • D. CR3+ > CH3Cl > CH3OH >CH3OCH3

4. Rank the following in order of decreasing leaving group ability: H2O, HO–, Br–, H–

  • A. H2O > Br– > HO– > H–
  • B. H2O > HO– > Br– > H–
  • C. HO– > Br– > H2O > H–
  • D. HO– > H– > H2O > Br–

5. Rank the following in order of decreasing oxidation state: amine, carboxylic acid, aldehyde, alkane

  • A. Aldehyde, amine, alkane, carboxylic acid
  • B. Carboxylic acid, aldehyde, amine, alkane
  • C. Carboxylic acid, amine, aldehyde, alkane
  • D. Alkane, amine, aldehyde, carboxylic acid

6. If cinnamaldehyde was treated with LiAlH4, what reaction would occur?

  • A. Reduction, resulting in a primary alcohol
  • B. Oxidation, resulting in a carboxylic acid
  • C. An acid–base reaction, resulting in a diol
  • D. No reaction would occur

7. If 2-butanol was treated with dichromate, what reaction would occur?

  • A. Reduction, resulting in the formation of butene
  • B. Oxidation, resulting in the formation of butanoic acid
  • C. Oxidation, resulting in the formation of butanone
  • D. No reaction would occur

8. If 1-hexanol was treated with pyridinium chlorochromate, what would the end product be?

  • A. 2-hexanol
  • B. 2-hexanone
  • C. Hexanal
  • D. Hexanoic acid

9. SN1 reactions show first-order kinetics because:

  • A. the rate-limiting step is the first step to occur in the reaction.
  • B. the rate-limiting step involves only one molecule.
  • C. there is only one rate-limiting step.
  • D. the reaction involves only one molecule.

10. In a protic solvent, which of the following halogens would be the best nucleophile?

  • A. Br–
  • B. Cl–
  • C. F–
  • D. I–

11. Which of the compounds below can undergo oxidation?

  • A.
  • B.
  • C.
  • D.

12. Treatment of (S)-2-bromobutane with sodium hydroxide results in the production of a compound with an (R) configuration. This reaction has most likely taken place through:

  • A. an SN1 mechanism.
  • B. an SN2 mechanism.
  • C. an SN1 and SN2 mechanism in sequence.
  • D. an SN1 and SN2 mechanism simultaneously.

13. Which of the following solvents would be LEAST useful for a nucleophile–electrophile reaction?

  • A. H2O
  • B. CH3CH2OH
  • C. CH3SOCH3
  • D. CH3CH2CH2CH2CH2CH3

14. Aldehydes are generally more reactive than equivalent ketones to nucleophiles. This is likely due to differences in:

  • A. steric hindrance.
  • B. leaving-group ability.
  • C. resonance stabilization.
  • D. electron-withdrawing character.

15. Which conversion between carboxylic acid derivatives is NOT possible by nucleophilic reaction?

  • A. Carboxylic acid to ester
  • B. Ester to carboxylic acid
  • C. Anhydride to amide
  • D. Ester to anhydride