AIIMS2019Chemistry-Organic Chemistry

AIIMS 2019 Chemistry SN₁ Reactions MCQ Question

Type: MCQ-conceptual-Medium-Class 11

The compound most reactive towards SN1\text{S}_\text{N}1 reaction is:

A

MeCOCH2Cl\text{MeCOCH}_2\text{Cl}

B

MeOCH2Cl\text{MeOCH}_2\text{Cl}

C

C6H5CH2CH2Cl\text{C}_6\text{H}_5\text{CH}_2\text{CH}_2\text{Cl}

Correct Answer

Option B

Detailed Explanation

In the SN₁ reaction, the intermediate (i) MeO⁺CH₂ is a carbocation where the positive charge is on the oxygen atom, which is less stable due to its high electronegativity and inability to stabilize a positive charge effectively. In contrast, structure (ii) Me⁻O⁺=CH₂, although it has a positive charge on oxygen, features a double bond to carbon, allowing for better charge delocalization and stabilization through resonance. Therefore, the statement that structure (ii) is more stable than (i) is false, making option B correct. Options A and C are incorrect as they misinterpret the stability of the intermediates, while option D does not apply since the answer is clearly established.

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