Which of the following gem diols is stable?
Correct answer: C. Option C: Gem diol with a strong electron-withdrawing group
- A. Option A: Gem diol with no electron-withdrawing groups
- B. Option B: Gem diol with a weak electron-withdrawing group
- C. Option C: Gem diol with a strong electron-withdrawing group
- D. Option D: Gem diol with a bulky substituent
Explanation
The stability of a geminal diol is significantly influenced by the presence of electron-withdrawing groups attached to the carbon that bears the hydroxyl groups. These groups stabilize the diol by enhancing the electrophilic character of the carbon, making it less likely for the diol to revert to the carbonyl compound. In Option C, the gem diol is stabilized by a strong electron-withdrawing group, which makes it the most stable among the options provided. In contrast, Options A and B lack sufficient electron-withdrawing character to stabilize the gem diol, and Option D introduces steric hindrance, which can destabilize the diol.
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About Reactivity of Aldehydes and Ketones
The polar carbonyl group makes aldehydes and ketones undergo nucleophilic addition, reduction and condensation reactions. Aldehydes are generally more reactive and oxidise readily to carboxylic acids, whereas ketones resist mild oxidation; reactions with hydrogen cyanide, sodium bisulfite and 2,4-DNP help identify their behaviour.
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