Practice problems chapter 15

1) Which of the following structures contribute(s) to the resonance hybrid of the intermediate
formed when acetanilide undergoes para-bromination?

a) I
b) II
c) III
d) IV
e) All of these choices.

Answer: E

2) Which of the following contributors to the resonance stabilized hybrid formed when aniline
undergoes para-chlorination would be exceptionally stable?

a) I
b) II
c) III
d) IV
e) None of these choices.

Answer: B

3) Which of these liquids would be unsuitable as an inert solvent for a Friedel-Crafts reaction?

a) Chlorobenzene
b) Nitrobenzene
c) Acetophenone
d) (Trifluoromethyl) benzene
e) All of these choices could be used.

Answer: A
4) This substituent deactivates the benzene ring towards electrophilic substitution but directs the
incoming group chiefly to the ortho and para positions.

a) -OCH​2​CH​3
b) -NO​2
c) -F
d) -CF​3
e) -NHCOCH​3

Answer: C

5) This molecule ​does not normally​ participate as a reactant in a Friedel-Crafts reaction.

a) Benzene
b) Chlorobenzene
c) Nitrobenzene
d) Toluene
e) ​tert​-Butylbenzene

Answer: C

6) What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and HF?

a) butylbenzene
b) 2-phenylbutane
c) 2-methyl-1-phenylpropane
d) ​t-​butylbenzene
e) 2,2-diphenylbutane

Answer: B

7) A mixture of chlorobenzene (1 mol) and anisole (1mol) is allowed to react with Br​2​ (0.5 mol)
in the presence of trace amounts of FeBr​3​. What is the principal product of the competing
reactions?

a) 1-bromo-4-chlorobenzene
b) 1-bromo-2-chlorobenzene
c) 1-bromo-3-chlorobenzene
d) 4-bromoanisole
e) 3-bromoanisole

Answer: D

8) Which of the following reactions could be used to synthesize ​tert​-butylbenzene?

a)

b)

c)
d) All of these choices.
e) None of these choices.

Answer: D

9) Consider the following reaction: what is the expected product?

a) I
b) II
c) III
d) IV
e) V

Answer: B
10) Which of the following reactions would produce isopropylbenzene?

a)

b)

c)

d)
e) All of these choices.

Answer: E

11) Which of the following reactions would give the product(s) indicated in substantial amounts
(i.e., in greater than 50% yield)?
IV. None

Ans D

12) The major product(s) of the following reaction,

would be:

a) I
b) II
c) III
d) IV
e) V

Answer: E

13) What would be the product of the following reaction sequence?

a) I
b) II
c) III
d) IV
e) V

Answer: E

14) What would you expect to be the major product obtained from the following reaction?

a) I
b) II
c) III
d) IV
e) V

Answer: E

15) The major product(s), A, of the following reaction,

would be:

a) I
b) II
c) A mixture of I and II.
d) III
e) IV

Answer: E

16) What would you expect to be the major product obtained from the following reaction?
a) I
b) II
c) III
d) IV
e) V

Answer: E

17) Toluene is subjected to the action of the following reagents in the order given: (1)
KMnO​4​,OH​-​, heat; then H​3​O​+​ (2) HNO​3​, H​2​SO​4​ (3) Br​2​, FeBr​3
What is the final product of this sequence?

a) I
b) II
c) III
d) IV
e) V

Answer: A

18) What product would result from the following series of reactions,

a) I
b) II
c) III
d) IV
e) V

Answer: D

19) Arrange the following compounds in order of ​decreasing​ reactivity in electrophilic

substitution:
a) V > II > I > III > IV
b) II > V > III > I > IV
c) IV > I > III > V > II
d) III > II > I > IV > V
e) IV > V > II > I > III

Answer: B

20) Which of the following carbocations would be most stable?

a)

b)

c)

d)

e)

Answer: E