19. Reactions of Aromatics: EAS and Beyond

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

e. 3-methyl-1-phenylbutane

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

f. 1-phenyl-2,2-dimethylpropane

Predict the products formed when cyclohexanecarbaldehyde reacts with the following reagents.

(f) zinc amalgam and dilute hydrochloric acid

Predict the major products of the following reactions:

(a)

Predict the major products of the following reactions.

(c) o-xylene + H₂ (1000 psi, 100 °C, Rh catalyst)

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

a.

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

b.