Question

Which of the following compounds will give racemic mixture on nucleophilic substitution by $OH^{-}$ion?

(I) $CH_{3} - \underset{\underset{C_{2}H_{5}}{|}}{CH} - Br$ (II)

(III) $CH_{3} - \underset{\underset{C_{2}H_{5}}{|}}{CH} - CH_{2}Br$

• A. (I)
• B. (I), (II), (III)
• C. (II), (III)
• D. (I), (III)

Answer 1

Answer: (A)

(I)

Answer 2

Benzylic halides show high reactivity towards the $S_{N}1$reaction

The carbocation thus formed gets stabilized through resonance as shown in the figure.