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Question

Select the correct options with respect to the reaction of cis-3-methylcyclopentanol with SOCl2:

A
The reaction is SN1
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B
The reaction is SN2
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C
The reaction is an intramolecular nucleophilic substitution
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D
The reaction is E1cB
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Solution

The correct option is C The reaction is an intramolecular nucleophilic substitution
The alcohol (substrate) is secondary; with SOCl2, it undergoes an intramolecular nucleophilic substitution with retention of configuration at the carbinol carbon. The mechanism is sometimes called SNi.

Observe how the configuration is retained where the intramolecular substitution happens!

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