Chapter 16, Problem 50P

For each of the following substituted benzenes: [1] ${\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{Br}$; [2] ${\text{C}}_{\text{6}}{\text{H}}_{\text{5}}\text{CN}$; [3] ${\text{C}}_{\text{6}}{\text{H}}_{\text{5}}{\text{OCOCH}}_{\text{3}}$:

a. Does the substituent donate or withdraw electron density by an inductive effect?

b. Does the substituent donate or withdraw electron density by a resonance effect?

c. On balance, does the substituent make a benzene ring more or less electron rich than benzene itself?

d. Does the substituent activate or deactivate the benzene ring in electrophilic aromatic substitution?