Question

I am having a hard time understanding what to look for with this question. Do you have any tips or ways to memorize one over the other?
2. Consider these four benzene derivatives and answer the following questions. (8 points) A D E och o odcho Nos o och a. Which one would be most reactive in an electrophilic aromatic substitution reaction? b. Which one would be least reactive in an electrophilic aromatic substitution reaction? c. Which one would be most reactive in a nucleophilic aromatic substitution reaction? d. Which one would be most reactive in a nucleophilic acyl substitution reaction?

Answer 1

rate of electrophilic aromatic subsititution (EAS) is directly proportional to electron density of aromatic ring. the more electron rich the substrate is more will the rate of electrophilic substitution

reverse is the true for nucleophilic substitution. Electron deficient system is easily attacked by nucleophile 3

COOCH3 shows -M

OCOCH3 shows +M

OMe shows +M

NO2 shows - M

Br shows -I

A. D is most reactive toward EAS because of+M of Ome

B. C is least reactive toward EAS because of -M of No2 and -I of Br

C. D is least reactive toward nucleophilic substitution because of+M of Ome

D. C is most reactive toward nucleophilic substitution because of -M of No2 and -I of Br