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문제 36
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)
문제 37
Propose a mechanism for the reaction of benzyl bromide with ethanol to give benzyl ethyl ether.
문제 38a,b
(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.
문제 38c,d
(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.
문제 39a
Show how you would synthesize the following compounds, using the indicated starting materials.
(a) 3-phenylbutan-1-ol from styrene
문제 40
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.
문제 41a
Predict the products formed when m-cresol (m-methylphenol) reacts with
(a) NaOH and then ethyl bromide
문제 41b
Predict the products formed when m-cresol (m-methylphenol) reacts with
(b) acetyl chloride,
문제 41c
Predict the products formed when m-cresol (m-methylphenol) reacts with
(c) bromine in CCl4 in the dark
문제 42
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
문제 43a
Predict the major product at the end of each sequence.
(a)
문제 43b
Predict the major product at the end of each sequence.
(b)
문제 44
Predict the site(s) of electrophilic attack on these compounds.
문제 45
Predict the products.
문제 46
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.
문제 47
Propose a synthetic sequence of this trisubstituted benzene starting from toluene.
문제 49
Starting from toluene, propose a synthesis of this trisubstituted benzene.
문제 50a,b
Predict the major products formed when benzene reacts (just once) with the following reagents.
a. tert-butyl bromide, AlCl3
b. 1-chlorobutane, AlCl3
문제 50c
Predict the major products formed when benzene reacts (just once) with the following reagents.
c. isobutyl alcohol + BF3
문제 50d
Predict the major products formed when benzene reacts (just once) with the following reagents.
d. bromine + a nail
문제 50e
Predict the major products formed when benzene reacts (just once) with the following reagents.
e. isobutylene + HF
문제 50f
Predict the major products formed when benzene reacts (just once) with the following reagents.
f. fuming sulfuric acid
문제 50g
Predict the major products formed when benzene reacts (just once) with the following reagents.
(g) 1-chloro-2,2-dimethylpropane + AlCl3
문제 50h
Predict the major products formed when benzene reacts (just once) with the following reagents.
(h) benzoyl chloride + AlCl3
문제 50i
Predict the major products formed when benzene reacts (just once) with the following reagents.
(i) iodine + HNO3
문제 50j
Predict the major products formed when benzene reacts (just once) with the following reagents.
(j) nitric acid + sulfuric acid
문제 50k,l
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
문제 52a
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
문제 52b
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
문제 53a
Predict the major products of the following reactions.
(a) 2,4-dinitrochlorobenzene + NaOCH3
