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)

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

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

Predict the products of the following electrophilic aromatic substitution reactions.

(b)

Predict the major product of the following electrophilic aromatic substitution reactions.

(c)

Would you expect chlorination to occur ortho, para, or meta to the pyridinium ion in the following molecule? Explain your answer.

Protonation of aniline slows electrophilic aromatic substitution and directs electrophiles to the meta position. Why?