Show how you would synthesize the following aromatic derivatives from benzene.

a. p-tert-butylnitrobenzene

Show how you would synthesize the following aromatic derivatives from benzene.

b. p-toluenesulfonic acid

Show how you would synthesize the following aromatic derivatives from benzene.

c. p-chlorotoluene

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.

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

c.

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

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

g. n-butylbenzene

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

h.

Propose a mechanism that shows why p-chlorotoluene reacts with sodium hydroxide at 350 °C to give a mixture of p-cresol and m-cresol.

Propose mechanisms and show the expected products of the following reactions.

(a) 2,4-dinitrochlorobenzene + sodium methoxide (NaOCH₃)

(b) 2,4-dimethylchlorobenzene + sodium hydroxide, 350 °C

Propose mechanisms and show the expected products of the following reactions.

(c) p-nitrobromobenzene + methylamine (CH₃–NH₂)

(d) 2,4-dinitrochlorobenzene + excess hydrazine (H₂N–NH₂)

The highly reactive triple bond of benzyne is a powerful dienophile. Predict the product of the Diels–Alder reaction of benzyne (from chlorobenzene and NaOH, heated) with cyclopentadiene.

What products would you expect from the following reactions?

(a)

(b)

What organocuprate reagent would you use for the following substitutions?

(a)

(b)

What products would you expect from the following reactions?

(a)

What products would you expect from the following reactions?

(b)

What substituted alkene would you use in the Heck reaction to make the following products?

(a)

(b)

What products would you expect from the following Suzuki coupling reactions?

(a)

What products would you expect from the following Suzuki coupling reactions?

(b)

Show how you would use Suzuki reactions to synthesize these products from the indicated starting materials. You may use any additional reagents you need.

(a)

Show how you would use Suzuki reactions to synthesize these products from the indicated starting materials. You may use any additional reagents you need.

(b)

Propose mechanisms for the Birch reduction of benzoic acid. Show why the observed orientation of reduction is favored in each case.

Propose mechanisms for the Birch reduction of anisole. Show why the observed orientation of reduction is favored in each case.

Predict the major products of the following reactions.

(a) toluene + excess Cl₂ (heat, pressure)

Predict the major products of the following reactions.

(b) benzamide (PhCONH₂) + Na (liquid NH₃, CH₃CH₂OH)

Predict the major products of the following reactions.

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

Predict the major products of the following reactions.

(d) p-xylene + Na (liquid NH₃, CH₃CH₂OH)

(e)

Predict the major products of treating the following compounds with hot, concentrated potassium permanganate, followed by acidification with dilute HCl.

(a) isopropylbenzene

(b) p-xylene

(c)

Propose a mechanism for the bromination of ethylbenzene shown below.