MCAT Organic Chemistry Question 115: Answer and Explanation
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Question: 115
10. The α-hydrogen of a carboxylic acid is:
I. more acidic than the hydroxyl hydrogen.
II. less acidic than the hydroxyl hydrogen.
III. very acidic, as organic compounds go.
- A. I only
- B. II only
- C. I and III only
- D. II and III only
Correct Answer: D
Explanation:
The α-hydrogen of a carboxylic acid is quite acidic as far as organic compounds go, due to resonance stabilization. However, the hydroxyl hydrogen is significantly more acidic because it is able to share the negative charge resulting from deprotonation between both electronegative oxygen atoms in the functional group.