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Question

Which of alkyl halides exhibits complete racemisation in SN1 reaction?

A
(CH)3CCl
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B
CH3CH2CH2Cl
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C
CH3CH2Cl
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D
C6H5CH2Cl
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Solution

The correct option is A C6H5CH2Cl
All the molecules undergoing SN1 reaction shows racemisation as there is formation of 2 types of product in equal amount. Out of all these 4 alkyl halides , C6H5CH2Cl i.e benzylic chloride has the strongest tendency to undergo SN1 here thus leading to formation of racemic mixture as it contains benzylic carbocation which is most stable.

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