Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:
a. benzene, ethylbenzene, chlorobenzene, nitrobenzene, anisole

Predict the major products of the following reactions.

(c) nitrobenzene + fuming sulfuric acid

In Chapter 23, we learned about the electrophilic aromatic nitration reaction. When phenol is subjected to these conditions with a large excess of nitric acid, a molecule called picric acid is produced. Predict the product of this reaction and explain why the pK_a value of this compound is 0.38.

Predict the major products of the following reactions.

(b) phenol + tert-butyl chloride + AlCl₃

b. Rank the same compounds from greatest tendency to least tendency to undergo electrophilic aromatic substitution.

chlorobenzene, 1-chloro-2,4-dinitrobenzene, p-chloronitrobenzene

For each horizontal row of substituted benzenes, indicate

c. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction.

1.

2.

For each horizontal row of substituted benzenes, indicate

c. the one that yields the highest percentage of meta product in an electrophilic aromatic substitution reaction.

3.

Are the following substituents ortho–para directors or meta directors?

a. CH=CHC≡N 

b. NO₂ 

c. CH₂OH

Draw the resonance contributors for:

a. benzaldehyde