Question

$\underset{Specificrotaion=+{50}^o}{Ph-CH\left(OH\right){CH}_3}\underset{}{\overset{SO{Cl}_2}{\to }}\underset{|Cl}{PhCl}-{CH}_3$
Which of the following mechanisms does the reaction proceed?

• A. $S_{N}i$
• B. ${S_N}^2$
• C. ${S_N}^1$
• D. $E_2$

Answer 1

Answer: (C)

${S_N}^1$

The reaction proceeds through $S{N}^1$ mechanism. The $-OH$ group of optically active substrate is replaced with $-Cl$ atom to form racemic mixture as the specific rotation of substrate is mentioned but that of product is not mentioned.