MCAT Organic Chemistry Question 66: Answer and Explanation
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Question: 66
6. Which of the following correctly lists hexanol, phenol, and cyclohexanol by increasing acidity of the hydroxyl hydrogen?
- A. Phenol < hexanol < cyclohexanol
- B. Cyclohexanol < hexanol < phenol
- C. Cyclohexanol < phenol < hexanol
- D. Phenol < cyclohexanol < hexanol
Correct Answer: B
Explanation:
Phenols have significantly more acidic hydroxyl hydrogens than other alcohols, so this will be the most acidic hydroxyl hydrogen. The acidity of hexanol and cyclohexanol are close, but the hydroxyl hydrogen of hexanol is slightly more acidic because the ring structure of cyclohexanol is slightly electron-donating, which makes its hydroxyl hydrogen slightly less acidic.