Question

Benzylamine may be alkylated as shown in the following equation :

$C_{6}H_{5}CH_{2}NH_{2} + R - X\overset{\quad\quad}{\rightarrow}C_{6}H_{5}CH_{2}NHR$

Which of the following alkyl halides is best suited for this reaction through $S_{N}1$mechanism?

• A. $CH_{3}Br$
• B. $C_{6}H_{5}Br$
• C. $C_{6}H_{5}CH_{2}Br$
• D. $C_{2}H_{5}Br$

Answer 1

Answer: (C)

$C_{6}H_{5}CH_{2}Br$

Answer 2

: $C_{6}H_{5}CH_{2}Br$is best suited for this reaction through $S_{N}1$mechanism as the carbocation $(C_{6}H_{5}CH_{2})$ formed is resonance stabilized.