Question

Select the correct options with respect to the reaction of cis-3-methylcyclopentanol with $SOC{l}_2$:

• A. The reaction is $S_{N}1$
• B. The reaction is $S_{N}2$
• C. The reaction is an intramolecular nucleophilic substitution
• D. The reaction is $E_{1}cB$

Answer 1

The correct option is C The reaction is an intramolecular nucleophilic substitution

The alcohol (substrate) is secondary; with $SOC{l}_2$, it undergoes an intramolecular nucleophilic substitution with retention of configuration at the carbinol carbon. The mechanism is sometimes called $S_{N}i$.

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