Chapter 23, Problem 52P

Draw the products formed when $p\text{-}$ methylaniline $\left(p{\text{-CH}}_{\text{3}}{\text{C}}_{\text{6}}{\text{H}}_{\text{4}}{\text{NH}}_{\text{2}}\right)$ is treated with each reagent.

a. $\text{HCl}$

b. ${\text{CH}}_{\text{3}}\text{COCl}$

c. ${\left({\text{CH}}_{\text{3}}\text{CO}\right)}_{\text{2}}\text{O}$

d. excess ${\text{CH}}_{\text{3}}\text{I}$

e. ${\left({\text{CH}}_{\text{3}}\right)}_{\text{2}}\text{C}-\text{O}$

f. ${\text{CH}}_{\text{3}}\text{COCl,}{\text{AlCl}}_{\text{3}}$

g. ${\text{CH}}_{\text{3}}{\text{CO}}_{\text{2}}\text{H}$

h. ${\text{NaNO}}_{\text{2}}\text{,}\text{HCl}$

i. Part (b), then ${\text{CH}}_{\text{3}}\text{COCl,}{\text{AlCl}}_3$

j. ${\text{CH}}_{\text{3}}\text{CHO,}{\text{NaBH}}_{\text{3}}\text{CN}$