19. Reactions of Aromatics: EAS and Beyond

Show the mechanism for the generation of the acylium ion if an acid anhydride is used instead of an acyl chloride for the source of the acylium ion.

What are the products of the following reactions?

c.

d.

Show how Friedel–Crafts acylation might be used to synthesize the following compounds.

a. acetophenone

Show how Friedel–Crafts acylation might be used to synthesize the following compounds.

b. benzophenone

Show how Friedel–Crafts acylation might be used to synthesize the following compounds.

c. n-butylbenzene

Show how you would use the Friedel–Crafts acylation, Clemmensen reduction, and/or Gatterman–Koch synthesis to prepare the following compounds:

c.

Predict the major products formed when benzene reacts (just once) with the following reagents.

(k) carbon monoxide, HCl, and AlCl₃/CuCl

(l) CH₂(COCl)₂, AlCl₃

Predict the major products of the following reactions.

(d) nitrobenzene + acetyl chloride + AlCl₃

Predict the major products of the following reactions.

(e) p-methylanisole + acetyl chloride + AlCl₃

Draw the product(s) of each of the following reactions:

c. p-xylene + acetyl chloride + AlCl₃ followed by H₂O

Show two pairs of reagents that would each result in formation of the following compound: