Question

The major product in the following reaction

• A. A) ortho-chlorobenzyl alcohol
• B. B) 4-chlorobenzyl chloride
• C. C) benzyl chloride
• D. D) ortho-chlorobenzyl chloride

Answer 1

Answer: (B)

B) 4-chlorobenzyl chloride

Answer 2

The reaction involves both nucleophilic substitution of the hydroxyl group and electrophilic aromatic substitution on the phenyl ring. The -CH2OH group is an ortho, para director. Para substitution is favored due to steric reasons, leading to 4-chlorobenzyl alcohol. This then reacts with HCl to substitute the hydroxyl group, forming 4-chlorobenzyl chloride. Alternatively, benzyl chloride is formed first, which then undergoes para-chlorination.