MCAT Organic Chemistry Question 163: Answer and Explanation

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Question: 163

13. In a molecule containing a carboxylic acid group, what would be expected in a ¹H–NMR spectrum?

A. A deshielded hydrogen peak for the hydroxyl hydrogen, shifted left
B. A deshielded hydrogen peak for the hydroxyl hydrogen, shifted right
C. A shielded hydrogen peak for the hydroxyl hydrogen, shifted left
D. A shielded hydrogen peak for the hydroxyl hydrogen, shifted right

Correct Answer: A

Explanation:

The oxygen of the hydroxyl group will deshield the hydroxyl hydrogen, shifting it downfield, or left. Hydrogens in carboxylic acids can have some of the most downfield absorbances, around 10.5 to 12 ppm.

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