Chapter 16: Q9 P (page 495)
Question: Predict the major products of the following reactions:
(a) Nitration of bromobenzene
(b) Bromination of nitrobenzene
(c) Chlorination of phenol
(d) Bromination of aniline
Short Answer
a.

b.

c.

d.

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Chapter 16: Q9 P (page 495)
Question: Predict the major products of the following reactions:
(a) Nitration of bromobenzene
(b) Bromination of nitrobenzene
(c) Chlorination of phenol
(d) Bromination of aniline
a.

b.

c.

d.

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Monobromination of toluene gives a mixture of three bromotoluene products. Draw and name them.
The sulfonation of an aromatic ring with is reversible. That is, heating benzenesulfonic acid with H2SO4 yields benzene. Show the mechanism of the desulfonation reaction. What is the electrophile?
Show the major product(s) from reaction of the following substances with
(1) , and
(2) , :
a.

b.

Which of the following alkyl halides would you expect to undergo Friedel–
Crafts reaction with rearrangement and which without? Explain.
(a)
(b)
(c)
(d)
(e) Chlorocyclohexane
Question: Use your knowledge of directing effects, along with the following data, to deduce the directions of the dipole moments in aniline and bromobenzene.

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