Chapter 18, Problem 18.36P

Draw the products formed when phenol $\left({\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{OH}\right)$ is treated with each set of reagents.

a. [1] ${\text{HNO}}_{\text{3}}\text{,}{\text{H}}_{\text{2}}{\text{SO}}_{\text{4}}$; [2] $\text{Sn,}\text{HCl}$

b. [1] ${\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\right)}_{\text{2}}\text{CHCOCl,}{\text{AlCl}}_3$; [2] $\text{Zn}\left(\text{Hg}\right)\text{,}\text{HCl}$

c. [1] ${\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\text{Cl,}{\text{AlCl}}_3$; [2] ${\text{Br}}_{\text{2}},hv$

d. [1] ${\left({\text{CH}}_{\text{3}}{\text{CH}}_{\text{2}}\right)}_{\text{2}}\text{CHCl,}{\text{AlCl}}_3$; [2] ${\text{KMnO}}_{\text{4}}$