MCAT Organic Chemistry Question 142: Answer and Explanation

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Question: 142

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

Correct Answer: D

Explanation:

One resonance structure of a C–N bond in an amide has the double bond between the C and N, not between the C and O. Thus, the C–N bond of an amide has some sp² character, and sp²-hybridized atoms exhibit planar geometry.

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