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Organic Chemistry Problem Solving

Practice Test III
(Chapter 12-Aromatic Compounds II)
Multiple Choice :
1. Which of the following groups are meta directors for electrophilic aromatic substitution
reactions?

O
NO 2

OCH 3

CH 3
I

OH

II

___A. II, III, IV

O
N C CH 3
H

III
___B. III, V, VI

IV

NH 2

___C. I, II, IV

___D. I, IV, VI

VI
___E. All the above

2. Which of the following would you expect to undergo bromination faster than benzene?
O
+

C CH

___A.

3.

___B.

N(CH 3 )3

___C.

___D.

What is the major product from the following reaction?

OCH 3

O
CH 3 C Cl
AlCl3

OCH 3

___A.

___C.

CH 3

___B.

OCH 3
O
C
CH 3

C
CH 3

OCH 3

O
C

___D.

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Cl

OCH 3

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4.

What is the major product from the following reaction?

CN
Br2
FeBr3
CN

CN
Br

___A. Br

___B.
CN

Br

___D. Br

___C.
5.

Which of the following is not formed in the reaction below?

H2SO 4 (conc)
CH 3

heat

NH 2

SO 3H
SO 3H

CH 3

CH 3

___A.

NH 2

___B.

NH 2

HO 3S
CH 3

___C.

HO 3S

NH 2

___D.

___E. All of these are formed in this reaction

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CH 3
NH 2

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6. Which di-substituted benzene compound reacts most readily (fastest) towards nitration?
___A. 4-bromo-1-methylbenzene

___B. p-isopropylphenol

___C. m-nitrotoluene

___D. m-hydroxyaniline

___E. 2-methyl-1-nitrobenzene

7. In the Friedel-Crafts acylation reaction:

____A. Polyacylations often occur due to ring activating effects of the acyl group.
____B. The acylium ion is relatively unstable so rearrangement products are always produced.
____C. Acid halides are the source of the acyl group.
____D. improved yields occur when the reaction is run with amino or nitro groups on the ring.
8.

Nitration of chlorobenzene occurs:

____A. faster than nitration of benzene and gives the ortho and para products.
____B. faster than nitration of benzene and gives the meta product.
____C. slower than nitration of benzene and gives the ortho and para products.
____D. slower than nitration of benzene and gives the meta product.
____E. slower than nitration of benzene and gives the ortho and meta products.

9.

What is a feature found in all ortho-para directing groups?

____A. An oxygen atom is directly attached to the aromatic ring.
____B. The group has the ability to stabilize the positive charge of the arenium ion.
____C. The atom attached to the aromatic ring possesses an unshared pair of electrons.
____D. The atom directly attached to the aromatic ring is more eletronegative than carbon.
____E. The group contains a multiple bond.

10.

In Friedel-Crafts alkylations of benzene, dialkylation is often a significant product. In

Friedel-Crafts acylations of benzene, diacylation is not a significant product. Why?
___A. Alkyl groups activate the ring to further substitution, acyl groups deactivate the ring.
___B. Alkyl groups are less sterically hindered than acyl groups.
___C. Acyl cations are more difficult to make with Lewis acids.
___D. Carbocations undergo rearrangements whereas acyl cations do not.

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11. Which isomer of dichlorobenzene gives a single product when nitrated?

Cl
Cl

Cl
Cl

Cl

___B.

___A.

Cl

___C.

___D. none of them

12. Arrange the following compounds in increasing order of their reactivity towards
electrophilic aromatic substitution (least reactive first).

O
O

Br

CH 3
A

CH 3
D

___A. A< C< D< B ___B. A< D< C< B ___C. C< A< B< D ___D. C< A< D< B
13.

Based on your knowledge of substituent effects in electrophilic aromatic substitution

reactions, predict the effect the substituent [-S(CH3)2]+ would have in EAS?
___A. ortho/para director & activator

___B. ortho/para director & deactivator

___C. meta director & activator

___D. meta director & deactivator

14. Which point on the reaction diagram corresponds to the species shown to the right for the
acylation of benzene?
A
C
O
B
+

C R
_
+
+ AlCl 4

G
D

Rx

____A.

____B.

____C.

____D.

15. How would you carry out the following synthesis? You may use any reagent(s) you wish

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16. Solve the following road map problem. Determine the products A-H

E C 6H11Br
H 2, pt
excess

2 Na (s)

Br 2
AlBr 3

2R-OH

G C 6H 8
1) O 3
2) Zn, H 2O

A C 6H 6

D C 6H5Br

CH 3-Br
AlBr 3

HNO 3
H 2SO 4

H 2C 3H4O 2
Strong IR absorptions
@ 2750 & 1715 cm-1

B C 7H 8

F C 7H7NO 2

Na 2Cr 2O 7
H 2SO 4

NaOH (aq)

O
C
O-Na+

C C 7H6O 2

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