Which of the following does not react with $N a H S O_{3}$ (sodium bisulphite)?

C H_{3} - O | | C - H

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C H_{3} - O | | C - E t

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E t - O | | C - E t

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P h - C H_{2} - O | | C - C H_{3}

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Solution

The correct option is B $E t - O | | C - E t$
$O$
Acetophenone $(p h - C H_{2} - | | C - C H_{3})$ do not give bisulphite test because of steric hindrance.
The nucleophilic addition to carbonyl group results in change of hybridisation in which substituents get closer. So, if there are bulky substituents nucleophilic addition is not favourable.

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C H_{3} - O | | C - C H_{3} (A), C H_{3} - O | | C - H (B), C H_{3} - O | | C - C H_{2} - C l (C), H - O | | C - H (D), C l - C H_{2} - O | | C - H (E)

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I

I I

I I I

C H_{2} = O H | C - C H_{2} (I) - O | | C - C H_{3} ⇌ C H_{3} - O | | C - C H_{2} (I I) - O | | C - C H_{3}

⇌ C H_{3} - O H | C = C H (I I I) - O | | C - C H_{3}

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