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Problem 41a
Predict the products formed when m-cresol (m-methylphenol) reacts with
(a) NaOH and then ethyl bromide
Problem 41b
Predict the products formed when m-cresol (m-methylphenol) reacts with
(b) acetyl chloride,
Problem 41c
Predict the products formed when m-cresol (m-methylphenol) reacts with
(c) bromine in CCl4 in the dark
Problem 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
Problem 43a
Predict the major product at the end of each sequence.
(a)
Problem 43b
Predict the major product at the end of each sequence.
(b)
Problem 44
Predict the site(s) of electrophilic attack on these compounds.
Problem 45
Predict the products.
Problem 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.
Problem 47
Propose a synthetic sequence of this trisubstituted benzene starting from toluene.
Problem 49
Starting from toluene, propose a synthesis of this trisubstituted benzene.
Problem 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
Problem 50c
Predict the major products formed when benzene reacts (just once) with the following reagents.
c. isobutyl alcohol + BF3
Problem 50d
Predict the major products formed when benzene reacts (just once) with the following reagents.
d. bromine + a nail
Problem 50e
Predict the major products formed when benzene reacts (just once) with the following reagents.
e. isobutylene + HF
Problem 50f
Predict the major products formed when benzene reacts (just once) with the following reagents.
f. fuming sulfuric acid
Problem 50g
Predict the major products formed when benzene reacts (just once) with the following reagents.
(g) 1-chloro-2,2-dimethylpropane + AlCl3
Problem 50h
Predict the major products formed when benzene reacts (just once) with the following reagents.
(h) benzoyl chloride + AlCl3
Problem 50i
Predict the major products formed when benzene reacts (just once) with the following reagents.
(i) iodine + HNO3
Problem 50j
Predict the major products formed when benzene reacts (just once) with the following reagents.
(j) nitric acid + sulfuric acid
Problem 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
Problem 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
Problem 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
Problem 53a
Predict the major products of the following reactions.
(a) 2,4-dinitrochlorobenzene + NaOCH3
Problem 53b
Predict the major products of the following reactions.
(b) phenol + tert-butyl chloride + AlCl3
Problem 53c
Predict the major products of the following reactions.
(c) nitrobenzene + fuming sulfuric acid
Problem 53d
Predict the major products of the following reactions.
(d) nitrobenzene + acetyl chloride + AlCl3
Problem 53e
Predict the major products of the following reactions.
(e) p-methylanisole + acetyl chloride + AlCl3
Problem 53f
Predict the major products of the following reactions.
(f) p-methylanisole + Br2 , light
Problem 54a
Predict the major products of bromination of the following compounds, using Br2 and FeBr3 in the dark.
(a)
