Question

Benzylamine may be alkylated as shown in the following equation:
$C_6{H}_{5}C{H}_{2}N{H}_2+R-X\to C_6{H}_{5}C{H}_{2}NHR$
Which of the following alkyl halides is best suited for this reaction through $S_{N}1$ mechanism?

• A. $C{H}_{3}Br$
• B. $C_6{H}_{5}Br$
• C. $C_6{H}_{5}C{H}_{2}Br$
• D. $C_2{H}_{5}Br$

Answer 1

The correct option is C $C_6{H}_{5}C{H}_{2}Br$

Since, $C_6{H}_{5}C{H}_{2}Br$ on ionization gives a resonance stabilized benzyl carbocation $\left(C_6{H}_{5}C{H}_2^{+}\right)$, therefore, $C_6{H}_{5}C{H}_{2}Br$ is the best suited for $S_{N}1$ reaction.