19. Reactions of Aromatics: EAS and Beyond

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) <IMAGE>

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

d. o-methylaniline + benzenediazonium chloride

Predict the products formed when m-cresol (m-methylphenol) reacts with (b) acetyl chloride,

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

<IMAGE>