Which of the following gem diols is stable?

C H_{3} - C (O H)_{2} - H

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C B r_{3} - C (O H)_{2} - H

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C F_{3} - C (O H)_{2} - H

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C_{6} H_{5} - C (O H)_{2} - C_{6} H_{5}

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Solution

The correct option is C $C F_{3} - C (O H)_{2} - H$
The presence of electron-withdrawing groups on alpha carbon atom stabilize the geminal diols.

$+ I$ group decreases stability of gem diol and hence decreases extent of hydration.

More is the $- I$ power of the group, more is the stability of geminal diols.

Intramolecular hydrogen bonding increases stability of gem diols. –I groups present on carbon having gem diol group increases strength of hydrogen bond.
More is the strength of hydrogen bond more will be the stability of gem diol.

Hence, option C is the correct answer.

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Similar questions

C_{6} H_{5} - C H_{3} | C | H - B r + H_{2} O ⟶ H O - C H_{3} | C | H - C_{6} H_{5} + H B r

C_{6} H_{5} - C H_{3} | C | H - B r + H_{2} O \to H O - C H_{3} | C | H - C_{6} H_{5} + H B r

C O H_{2}

C H_{3} - H

C H_{3} - C H_{2} - H

C H_{3} = C H - C H_{2} - H

C_{6} H_{5} - H

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