19. Reactions of Aromatics: EAS and Beyond

Predict the mononitration products of the following compounds.

d. p-methoxybenzoic acid

Predict the mononitration products of the following compounds.

e. m-cresol (m-methylphenol)

Predict the mononitration products of the following compounds.

f. o-hydroxyacetophenone

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

d. COOH

e. CF₃

f. N=O

Using resonance contributors for the carbocation intermediate, explain why a phenyl group is an ortho–para director.

For each of the following compounds, indicate the ring carbon(s) that is/are nitrated when the compound is treated with HNO₃/H₂SO₄:

e.

f.

a. Does a coupling reaction have to be used to synthesize p-dipropylbenzene?

b. Can a coupling reaction be used to synthesize p-dipropylbenzene?

What products are obtained from the reaction of the following compounds with one equivalent of Br₂, using FeBr₃ as a catalyst?

c.

d.

What are the products of the following reactions?

f.

Rank the following compounds from most reactive to least reactive in an electrophilic aromatic substitution reaction:

For each of the statements in Column I, choose a substituent from Column II that fits the description for the compound on the right:

<IMAGE>

Predict the site(s) of electrophilic attack on these compounds.

Predict the major products of bromination of the following compounds, using Br₂ and FeBr₃ in the dark.

(a)

Predict the major products of bromination of the following compounds, using Br₂ and FeBr₃ in the dark.

(b)

Predict the major products of bromination of the following compounds, using Br2 and FeBr3 in the dark.

(c)