Which of the following compounds would give the greatest yield of methylated?

Question

a. aniline
b. toluene
c. chlorobenzene
d. benzoic acid

Answer 1

Aniline, followed by toluene. Chlorobenzene is activated by resonance at the 2-, 4-, and 6-positions, but deactivated by induction, and so would be less active to methylation. Benzoic acid is deactivating, both by resonance and induction, and so would be least methylated.