MCAT Organic Chemistry Question 62: Answer and Explanation

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Question: 62

2. Tertiary alcohols are oxidized with difficulty because:

  • A. there is no hydrogen attached to the carbon with the hydroxyl group.
  • B. there is no hydrogen attached to the α-carbon of the carbonyl.
  • C. tertiary alcohols contain hydroxyl groups with no polarization.
  • D. they are relatively inert.

Correct Answer: A

Explanation:

Tertiary alcohols can be oxidized but only under extreme conditions because their carbon atoms do not have spare hydrogens to give up. Alcohol oxidation involves the removal of such a hydrogen so that carbon can instead make another bond to oxygen. If no hydrogen is present, a carbon–carbon bond must be cleaved, which requires a great deal of energy and will, therefore, occur only under extreme conditions. Choice (B) is incorrect because alcohols are not carbonyl-containing compounds. Choice (C) is incorrect because the hydroxyl group of the tertiary carbon is still polarized. Choice (D) is a false statement; tertiary alcohols are still involved in other reactions, such as an SN1 reaction.

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