Predict the major products when the following compounds are irradiated by light and treated with (1) 1 equivalent of Br₂ and (2) excess Br₂.

(a) isopropylbenzene

(b)

Propose a mechanism for the reaction of benzyl bromide with ethanol to give benzyl ethyl ether.

(a) Based on what you know about the relative stabilities of alkyl cations and benzylic cations, predict the product of addition of HBr to 1-phenylpropene.

(b) Propose a mechanism for this reaction.

(c) Based on what you know about the relative stabilities of alkyl radicals and benzylic radicals, predict the product of addition of HBr to 1-phenylpropene in the presence of a free-radical initiator.

(d) Propose a mechanism for this reaction.

Show how you would synthesize the following compounds, using the indicated starting materials.

(a) 3-phenylbutan-1-ol from styrene

The bombardier beetle defends itself by spraying a hot quinone solution from its abdomen. This solution is formed by the enzyme-catalyzed oxidation of hydroquinone by hydrogen peroxide. Write a balanced equation for this oxidation.

Predict the products formed when m-cresol (m-methylphenol) reacts with

(a) NaOH and then ethyl bromide

Predict the products formed when m-cresol (m-methylphenol) reacts with

(b) acetyl chloride,

Predict the products formed when m-cresol (m-methylphenol) reacts with

(c) bromine in CCl₄ in the dark

1,4-Benzoquinone is a good Diels–Alder dienophile. Predict the products of its reaction with

a. buta-1,3-diene

b. cyclopenta-1,3-diene

Predict the major product at the end of each sequence.

(a)

Predict the major product at the end of each sequence.

(b)

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

Predict the products.

To synthesize m-ethylbenzenesulfonic acid, a student attempted the Friedel–Crafts alkylation of benzenesulfonic acid with bromoethane. Do you predict that this reaction was successful? If not, propose an alternative synthesis.

Propose a synthetic sequence of this trisubstituted benzene starting from toluene.

Starting from toluene, propose a synthesis of this trisubstituted benzene.

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

a. tert-butyl bromide, AlCl₃

b. 1-chlorobutane, AlCl₃

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

c. isobutyl alcohol + BF₃

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

d. bromine + a nail

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

e. isobutylene + HF

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

f. fuming sulfuric acid

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

(g) 1-chloro-2,2-dimethylpropane + AlCl₃

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

(h) benzoyl chloride + AlCl₃

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

(i) iodine + HNO₃

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

(j) nitric acid + sulfuric acid

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

Show how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclic reagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures.

a. 1-phenyl-1-bromobutane

Show how you would synthesize the following compounds, starting with benzene or toluene and any necessary acyclic reagents. Assume para is the major product (and separable from ortho) in ortho, para mixtures.

b. 1-phenyl-1-methoxybutane

Predict the major products of the following reactions.

(a) 2,4-dinitrochlorobenzene + NaOCH₃