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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As written, the following syntheses have flaws. What is wrong with
each?


Triphenylmethane can be prepared by reaction of benzene and chloroform in the presence of . Propose a mechanism for the reaction.

At what position would you expect electrophilic substitution to occur in each of the following substances?
a.

b.

c.

Use Figure 16-11 to explain why Friedel–Crafts alkylations often give polysubstitution but Friedel–Crafts acylations do not.

Electrophilic substitution on 3-phenylpropanenitrile occurs at theortho and para positions, but reaction with 3-phenylpropenenitrileoccurs at the meta position. Explain, using resonance structures of theintermediates.

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