Chapter 16: Q7 P (page 493)
Identify the carboxylic acid chloride that might be used in a Friedel–Crafts acylation reaction to prepare each of the following acylbenzenes:
a.

b.

Short Answer
a.

b.

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Chapter 16: Q7 P (page 493)
Identify the carboxylic acid chloride that might be used in a Friedel–Crafts acylation reaction to prepare each of the following acylbenzenes:
a.

b.

a.

b.

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How many products might be formed on chlorination of o-xylene (o-dimethylbenzene), m-xylene, and p-xylene?
Would you expect the Friedel–Crafts reaction of benzene with (R)-2-chlorobutane to yield optically active or racemic product? Explain.
How would you synthesize the following substances starting from benzene or phenol? Assume that ortho- and para-substitution products can
be separated.
(a)o-Bromobenzoic acid (b)p-Methoxytoluene
(c)2,4,6-Trinitrobenzoic acid (d)m-Bromoaniline
Refer to Table 6-3 on page 170 for a quantitative idea of the stability of a benzyl radical. How much more stable (in kJ/mol) is the benzyl radical than a primary alkyl radical? How does a benzyl radical compare in stability to an allylradical?
The following molecular model of a dimethyl-substituted biphenyl represents the lowest-energy conformation of the molecule. Why are the two benzene rings tilted at a 63° angle to each other rather than being in the same plane so that their p orbitals overlap? Why doesn’t complete rotation around the single bond joining the two rings occur?

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