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.

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

Rank each group of compounds from most reactive to least reactive toward electrophilic aromatic substitution:

a. benzene, ethylbenzene, chlorobenzene, nitrobenzene, anisole

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.

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

Despite the amino group being an ortho/para director, nitration of aniline gives the meta isomer predominantly. Explain this result.

Predict the major product(s) that would result when molecules (a)–(i) are allowed to react under the following conditions. (iv) chlorocyclopentane, AlCl₃, (v) 1-chloro-1-methylcyclohexane , AlCl₃, (vi) PhCOCl, AlCl₃. If no reaction will occur, indicate by writing NR.

(a)