MCAT Organic Chemistry Question 154: Answer and Explanation
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Question: 154
4. Which of the following chemical shifts could correspond to an aldehydic proton signal in a 1H–NMR spectrum?
- A. 9.5 ppm
- B. 7.0 ppm
- C. 11.0 ppm
- D. 1.0 ppm
Correct Answer: A
Explanation:
The peak at 9.5 ppm corresponds to an aldehydic proton. This signal lies downfield because the carbonyl oxygen is electron-withdrawing and deshields the proton. Choice (C) corresponds to a carboxyl proton and is even further downfield because the acidic proton is deshielded to a greater degree than the aldehyde proton. Choice (B) corresponds to aromatic protons. Choice (D) is characteristic of an alkyl proton on an sp3-hybridized carbon.