Deck 4: Aromatic Compounds

Question 1

Which of the following structures accurately represents phenol?

A)
B)
C)
D)
E)

Answer 1

Question 2

How many different trisubstituted products are possible from the nitration of o-xylene?

A) 1
B) 2
C) 3
D) 4
E) 5

Answer 2

2

Question 3

Using the following monosubstituted benzene, which position would be meta to X?

A) 1
B) 2
C) 3
D) 4
E) 5

Answer 3

3

Question 4

What dibromobenzene can form only one tribromobenzene?

A) o-dibromobenzene
B) m-dibromobenzene
C) p-dibromobenzene
D) cumene
E) styrene

Question 5

Which of the following names represents more than one compound?

A) dichlorobenzene
B) 2-bromophenol
C) o-nitrobenzaldehyde
D) 2,4,6-trinitrotoluene
E) cumene

Question 6

Which name(s) of the following molecule is/are incorrect?

A) styrene
B) vinylbenzene
C) ethylbenzene
D) phenylethene
E) a and b

Question 7

Which of the following molecules is o-nitrophenol?

A)
B)
C)
D)
E)

Question 8

Which statement about benzene is true?

A) All six hydrogens in benzene are chemically equivalent.
B) Benzene decolorizes bromine solutions.
C) The molecule is planar, and each carbon is at the corner of a regular hexagon.
D) Both a and c are true.
E) Both b and c are true.

Question 9

Which of the following statements about benzene is FALSE?

A) the molecule is planar and each carbon is at a corner of regular hexagon
B) there are two resonance structures of equivalent energy
C) the bond angles are all 120º and the bond lengths are all 1.39Å
D) the typical mechanism by which reactions occur is by addition
E) each carbon in the benzene ring is sp² hybridized

Question 10

Which of the following is NOT an electrophile in an electrophilic aromatic substitution reaction?

A) NO₂⁺
B) (CH₃)₃C+
C) SO₃
D) Cl^-
E) all are

Question 11

Which alkylbenzene, C₉H₁₂, when nitrated can yield only one mononitro product?

A)
B)
C)
D)
E)

Question 12

The name of the following molecule is:

A) toluene
B) ethylbenzene
C) cumene
D) styrene
E) anisole

Question 13

The structural formula for p-chlorobenzoic acid is:

A)
B)
C)
D)
E)

Question 14

What is the name of the following molecule?
PhCH₂CH₂CH=CH₂

A) styrene
B) 4-phenyl-1-butene
C) 1-phenyl-3-butene
D) 3-benzyl-1-propene
E) allylbenzene

Question 15

The structure of chlorobenzene is correctly represented by:

A)
B)
C)
D)
E)

Question 16

What is the correct name for the following molecule?

A) o-bromobenzyl
B) biphenyl bromide
C) 2-bromodiphenylpropane
D) bromobenzylbenzene
E) o-benzylbromobenzene

Question 17

The correct name for is

A) 2-chloro-4-bromotoluene.
B) o-chloro-p-bromotoluene.
C) 1-bromo-3-chloro-4-methylbenzene.
D) 4-bromo-2-chlorotoluene.
E) m-chlorobromotoluene.

Question 18

Which position would be para to X?

A) 1
B) 2
C) 3
D) 4
E) 6

Question 19

In the mechanism for the nitration of benzene, what is the function of H₂SO₄?

A) to act solely as a solvent
B) to donate a proton to HNO₃
C) to accept a proton from HNO₃
D) to generate heat for reaction to occur
E) to protonate the benzene ring

Question 20

How many dinitrobenzoic acids are possible?

A) 4
B) 5
C) 6
D) 7
E) 8

Question 21

Which of the following groups are ortho, para-directing?

A) -CO₂CH₃
B) -CONH₂
C) -SO₃H
D)
E) -SCH₃

Question 22

The predominant intermediate in electrophilic nitration of toluene is:

A)
B)
C)
D)
E)

Question 23

The predominant product from sequential nitration and bromination of benzenesulfonic acid is:

A)
B)
C)
D)
E)

Question 24

If p-nitrophenol is treated with chlorine in the presence of AlCl₃, the only trisubstituted product observed is:

A) 2-chloro-4-nitrophenol
B) 3-chloro-4-nitrophenol
C) 3-chloro-5-nitrophenol
D) 4-chloro-2-nitrophenol
E) 4-chloro-3-nitrophenol

Question 25

What is the product of the following reaction?

A)
B)
C)
D)
E)

Question 26

The relative rates of nitration of the following are:

A) 1 > 2 > 3 > 4
B) 4 > 2 > 1 > 3
C) 2 > 1 > 4 > 3
D) 3 > 4 > 2 > 1
E) 3 > 2 > 1 > 4

Question 27

The only group among the following that is m-directing is:

A)
B)
C)
D)
E)

Question 28

The expected product from the following reaction is:

A)
B)
C)
D)

Question 29

In electrophilic aromatic substitution reactions, which of the following molecules are considered to be less reactive than benzene?

A)
B)
C)
D)
E)

Question 30

The predominant intermediate in the nitration of benzenesulfonic acid is:

A)
B)
C)
D)
E)

Question 31

Which of the following molecules is the most reactive toward electrophilic aromatic substitution?

A)
B)
C)
D)
E)

Question 32

Which electrophile is used to make acetophenone from benzene?

A)
B)
C)
D)
E)

Question 33

What is the name of the major product from the following sequence of reactions?

A) aniline
B) anisole
C) benzoic acid
D) phenol
E) toluene

Question 34

What is the best sequence of reactions to synthesize m-nitrophenol?

A)
B)
C)
D)
E)

Question 35

The name of the product of the following reaction is:

A) benzenesulfonic acid
B) aniline
C) benzoic acid
D) nitrobenzene
E) anisole

Question 36

The predominant product from the sequential bromination and nitration of benzene is:

A)
B)
C)
D)
E)

Question 37

Among the following groups, which ones are o,p-directing?

A) 1, 3, and 5
B) 1 and 5
C) 2 and 4
D) 2, 3, and 4
E) 1 and 3

Question 38

Which of the following groups is a meta director?

A) -Cl
B) -COOH
C) -OCH₃
D) -OH
E) -NH₂

Question 39

Which group is both ortho-para directing and ring-deactivating?

A) -Cl
B) -CH₃
C) -NO₂
D) -CHO
E) -OCH₃

Question 40

What is the final product of the following reaction sequence?

A)
B)
C)
D)
E)

Question 41

Which is the best reaction sequence to synthesize m-bromobenzenesulfonic acid from benzene?

A) 1) Br₂, AlBr₃, 2) H₂SO₄, SO₃
B) 1) H₂SO₄, SO₃ 2) Br₂, AlBr₃
C) 1) ethene, HF, 2) Br₂, AlBr₃
D) 1) CH₃Cl, AlCl₃, 2) Br₂, AlBr₃
E) 1) Br₂, AlBr₃, 2) CH₃COCl, AlCl₃

Question 42

The number of possible mononitration products of anthracene is:

A) 1
B) 2
C) 3
D) 4
E) 5

Question 43

The polycyclic aromatic hydrocarbon benzo[a]pyrene is a known carcinogen found in soot and tobacco smoke.What is its structure?

A)
B)
C)
D)
E)

Question 44

Which is the best reaction sequence to synthesize p-bromobenzenesulfonic acid from benzene?

A) 1) Br₂, AlBr₃, 2) H₂SO₄, SO₃
B) 1) H₂SO₄, SO₃, 2) Br₂, AlBr₃
C) 1) CH₃Cl, AlCl₃, 2) Br₂, AlBr₃
D) 1) Br₂, AlBr₃, 2) CH₃COCl, AlCl₃
E) 1) HBr, ethane, 2) H₂SO₄, SO₃

Question 45

A common polycyclic aromatic hydrocarbon is named naphthalene.What is the structure of naphthalene?

A)
B)
C)
D)
E)

Question 46

Which is the best sequence of reagents to use in synthesizing 2-chloro-4-nitrotoluene from benzene:

A) Cl₂, FeCl₃; then CH₃Cl, AlCl₃; then HNO₃, H₂SO₄
B) CH₃Cl, AlCl₃; then Cl₂, FeCl₃; then HNO₃, H₂SO₄
C) CH₃Cl, AlCl₃; then HNO₃, H₂SO₄; then Cl₂, FeCl₃
D) SO₃, H₂SO₄; then HNO₃, H₂SO₄; then Cl₂, FeCl₃
E) HNO₃, H₂SO₄; then Cl₂, FeCl₃; then CH₃Cl, AlCl₃