Deck 14: Aromatic Compounds

Question 1

The correct name for the compound shown below is:

A)3,4-Dibromoaniline
B)2,4-Dibromoaniline
C)2,5-Dibromoaniline
D)3,6-Dibromoaniline
E)2,6-Dibromoaniline

Answer 1

2,5-Dibromoaniline

Question 2

The correct name for the compound shown below is:

A)o-nitroanisole
B)m-nitroanisole
C)p-nitroanisole
D)p-nitrotoluene
E)4-nitrophenol

Answer 2

p-nitroanisole

Question 3

Which of the following is NOT 2-bromo-5-nitrobenzoic acid?

A)I
B)II
C)III
D)IV
E)V

Answer 3

IV

Question 4

Aniline is the name commonly assigned to:

A)Hydroxybenzene
B)Aminobenzene
C)Methylbenzene
D)Ethylbenzene
E)Methoxybenzene

Question 5

The correct name for the compound shown below is:

A)m-bromoaniline
B)o-bromoaniline
C)p-bromoaniline
D)o-bromobenzyl amine
E)3-bromophenyl amine

Question 6

3-Bromo-4-nitroacetophenone is:

A)I
B)II
C)III
D)IV
E)V

Question 7

Phenol is the name commonly assigned to:

A)Hydroxybenzene
B)Aminobenzene
C)Methylbenzene
D)Ethylbenzene
E)Methoxybenzene

Question 8

Anisole is the name commonly assigned to:

A)Hydroxybenzene
B)Aminobenzene
C)Methylbenzene
D)Ethylbenzene
E)Methoxybenzene

Question 9

4-Chloro-3-nitro-benzaldehyde is:

A)I
B)II
C)III
D)IV
E)V

Question 10

4-Bromo-2-nitroaniline is:

A)I
B)II
C)III
D)IV
E)V

Question 11

2-Bromo-5-nitroaniline is:

A)I
B)II
C)III
D)IV
E)V

Question 12

2-Bromo-4-nitroaniline is:

A)I
B)II
C)III
D)IV
E)V

Question 13

2-Bromo-4-nitroaniline is:

A)I
B)II
C)III
D)IV
E)V

Question 14

Xylene is the name commonly assigned to:

A)Hydroxybenzene
B)Aminobenzene
C)Dimethylbenzene
D)Ethylbenzene
E)Methoxybenzene

Question 15

The correct name for the compound shown below is:

A)m-chlorophenol
B)o-chlorophenol
C)p-chlorophenol
D)o-chlorobenzyl alcohol
E)2-chlorophenyl alcohol

Question 16

The correct name for the compound shown below is:

A)3-bromobenzene
B)4-bromobenzene
C)m-bromobenzene
D)o-bromotoluene
E)bromomethylbenzene

Question 17

4-Amino-2-chlorophenol is:

A)I
B)II
C)III
D)IV
E)V

Question 18

Toluene is the name commonly assigned to:

A)Hydroxybenzene
B)Aminobenzene
C)Methylbenzene
D)Ethylbenzene
E)Methoxybenzene

Question 19

m-Chlorobenzenesulfonic acid is:

A)I
B)II
C)III
D)IV
E)V

Question 20

Cumene is the name commonly assigned to:

A)Hydroxybenzene
B)Aminobenzene
C)Ethylbenzene
D)Isopropylbenzene
E)Isobutylbenzene

Question 21

4-Amino-2-bromoanisole is:

A)I
B)II
C)III
D)IV
E)V

Question 22

Which of these is the single best representation for naphthalene?

A)I
B)II
C)III
D)IV
E)V

Question 23

Which dichlorobenzene might theoretically yield three mononitro products?

A)o-Dichlorobenzene
B)m-Dichlorobenzene
C)p-Dichlorobenzene
D)None of these choices.
E)All of these choices.

Question 24

How many different dibromophenols are possible?

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

Question 25

4-Amino-2-chlorobenzaldehyde is:

A)I
B)II
C)III
D)IV
E)V

Question 26

Which dibromobenzene can yield only one mononitro derivative?

A)o-Dibromobenzene
B)m-Dibromobenzene
C)p-Dibromobenzene
D)More than one of these choices.
E)None of these choices.

Question 27

How many different dihydroxybromobenzenes are possible?

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

Question 28

Which dibromobenzene can,in theory,yield three mononitro derivatives?

A)o-Dibromobenzene
B)m-Dibromobenzene
C)p-Dibromobenzene
D)All of these choices.
E)None of these choices.

Question 29

Which dihydroxybenzene can yield only one mononitro derivative?

A)o-Dihydroxybenzene
B)m-Dihydroxybenzene
C)p-Dihydroxybenzene
D)More than one of these choices.
E)None of these choices.

Question 30

How many different dichloronitrobenzenes are possible?

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

Question 31

How many monochloronaphthalenes are possible?

A)2
B)3
C)4
D)5
E)6

Question 32

Which reagent(s)would serve as the basis for a simple chemical test that would distinguish between benzene and 1-hexene?

A)NaOH in H₂O
B)Br₂ in CCl₄
C)AgNO₃ in C₂H₅OH
D)NaHSO₃ in H₂O
E)None of these choices.

Question 33

The complete name for the following compound is:

A)sec-Hexylbenzene
B)2-Phenylhexane
C)(R)-2-Phenylhexane
D)(S)-2-Phenylhexane
E)Butylmethylphenylmethane

Question 34

4-Bromomethyl-2-nitroanisole is:

A)I
B)II
C)III
D)IV
E)V

Question 35

The complete name for the following compound is:

A)sec-Hexylbenzene
B)2-Phenylhexane
C)(R)-2-Phenylhexane
D)(S)-2-Phenylhexane
E)Butylmethylphenylmethane

Question 36

In theory,a single molecule of this compound will rotate plane-polarized light.

A)Butylbenzene
B)Isobutylbenzene
C)sec-Butylbenzene
D)tert-Butylbenzene
E)None of these choices.

Question 37

If thiophene is an aromatic molecule and reacts similarly to benzene,how many (neutral)monobromothiophenes could be obtained in the following reaction?

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

Question 38

How many dichloronaphthalenes are possible?

A)7
B)8
C)9
D)10
E)12

Question 39

3-Chloro-4-nitrobenzoic acid is:

A)I
B)II
C)III
D)IV
E)V

Question 40

Which is the only one of these reagents which will react with benzene under the specified conditions?

A)Cl₂,FeCl₃,heat
B)H₂,25 °C
C)Br₂/CCl₄,25 °C,dark
D)KMnO₄/H₂O,25 °C
E)H₃O⁺,heat

Question 41

Which reagent(s)would serve as the basis for a simple chemical test that would distinguish between naphthalene and 2,4,6-decatriene?

A)NaOH in H₂O
B)KMnO₄,OH^-,H₂O
C)NaBH₄,H₂O
D)H₂CrO₄
E)None of these choices.

Question 42

Which reagent(s)would serve as the basis for a simple chemical test that would distinguish between benzene and cyclohexene?

A)NaOH in H₂O
B)Br₂ in CCl₄
C)AgNO₃ in C₂H₅OH
D)NaHSO₃ in H₂O
E)None of these choices.

Question 43

In the molecular orbital model of benzene,how many $\pi$ -bonding molecular orbitals are there?

A)6
B)5
C)4
D)3
E)2

Question 44

In the molecular orbital model of benzene,how many pi electrons are delocalized about the ring?

A)2
B)3
C)4
D)5
E)6

Question 45

Recalling that benzene has a resonance energy of 152 kJ mol^-1 and naphthalene has a resonance energy of 255 kJ mol^-1,predict the positions which would be occupied by bromine when phenanthrene (below)undergoes addition of Br₂.

A)1,2
B)1,4
C)3,4
D)7,8
E)9,10

Question 46

Application of the polygon-and-circle technique reveals that single electrons occupy each of the two nonbonding orbitals in the molecular orbital diagram of:

A)Cyclobutadiene
B)Benzene
C)Cyclopropenyl cation
D)Cyclopentadienyl anion
E)Cycloheptatrienyl cation

Question 47

Which cyclization(s)should occur with an increase in pi-electron energy?

A)I
B)II
C)III
D)IV
E)All of these choices.

Question 48

In the molecular orbital model of benzene,the six p orbitals combine to form how many molecular orbitals?

A)6
B)5
C)4
D)3
E)2

Question 49

Why would 1,3-cyclohexadiene undergo dehydrogenation readily?

A)It is easily reduced.
B)Hydrogen is a small molecule.
C)1,3-Cyclohexadiene has no resonance energy.
D)It would gain considerable stability by becoming benzene.
E)It would not undergo dehydrogenation.

Question 50

Cyclopentadiene is unusually acidic for a hydrocarbon.An explanation for this is the following statement.

A)The carbon atoms of cyclopentadiene are all sp²-hybridized.
B)Cyclopentadiene is aromatic.
C)Removal of a proton from cyclopentadiene yields an aromatic anion.
D)Removal of a hydrogen atom from cyclopentadiene yields a highly stable free radical.
E)Removal of a hydride ion from cyclopentadiene produces an aromatic cation.

Question 51

In the molecular orbital model of benzene,how many pairs of degenerate $\pi$ -antibonding molecular orbitals are there?

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

Question 52

Which of the following statements about cyclooctatetraene is NOT true?

A)The compound rapidly decolorizes Br₂/CCl₄ solutions.
B)The compound rapidly decolorizes aqueous solutions of KMnO₄.
C)The compound readily adds hydrogen.
D)The compound is nonplanar.
E)The compound is comparable to benzene in stability.

Question 53

Which cyclization(s)should occur with a decrease in pi-electron energy?

A)I
B)II
C)III
D)IV
E)All of these choices.

Question 54

In the molecular orbital model of benzene,how many $\pi$ -antibonding molecular orbitals are there?

A)6
B)5
C)4
D)3
E)2

Question 55

In the molecular orbital model of benzene,how many pairs of degenerate $\pi$ -molecular orbitals are there?

A)6
B)5
C)4
D)3
E)2

Question 56

Which cyclization(s)should occur with an increase in pi-electron energy?

A)I
B)II
C)III
D)IV
E)All of these choices.

Question 57

Consider the molecular orbital model of benzene.In the ground state how many molecular orbitals are filled with electrons?

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

Question 58

In the molecular orbital model of benzene,how many pairs of degenerate $\pi$ -bonding molecular orbitals are there?

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

Question 59

Which cyclization(s)should occur with a decrease in pi-electron energy?

A)I
B)II
C)III
D)IV
E)All of these choices.

Question 60

In the molecular orbital model of benzene,how many pi electrons are in bonding molecular orbitals?

A)6
B)5
C)4
D)3
E)2

Question 61

In the molecular orbital model of 1,3-cyclobutadiene,how many electrons are in non-bonding molecular orbitals?

A)6
B)5
C)4
D)3
E)2

Question 62

In the molecular orbital model of the cyclobutadiene,how many pairs of degenerate $\pi$ -bonding molecular orbitals are there?

A)1
B)2
C)3
D)4
E)0

Question 63

In the molecular orbital model of the cyclopentadienyl cation,how many pairs of degenerate $\pi$ -bonding molecular orbitals are there?

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

Question 64

In the molecular orbital model of the cyclopentadienyl cation,how many pairs of degenerate $\pi$ -molecular orbitals are there?

A)6
B)5
C)4
D)3
E)2

Question 65

In the molecular orbital model of cyclobutadiene,how many non-bonding molecular orbitals are there?

A)1
B)2
C)3
D)4
E)0

Question 66

In the molecular orbital model of cyclobutadiene,how many $\pi$ -bonding molecular orbitals are there?

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

Question 67

In the molecular orbital model of which of the following substance(s)are non-bonding orbitals found?

A)1,3-Cyclobutadiene
B)Cyclopentadienyl anion
C)1,3,5,7-Cyclooctatetraene
D)Two of these choices.
E)All of these choices.

Question 68

Consider the molecular orbital model of cyclopentadienyl anion.In the ground state how many molecular orbitals are filled with electrons?

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

Question 69

In the molecular orbital model of the cyclopentadienyl cation,how many pairs of degenerate $\pi$ -antibonding molecular orbitals are there?

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

Question 70

In the molecular orbital model of cyclopentadienyl anion,how many pi electrons are delocalized about the ring?

A)2
B)3
C)4
D)5
E)6

Question 71

In the molecular orbital model of cycloheptadienyl cation,how many pi electrons are delocalized about the ring?

A)6
B)5
C)4
D)3
E)2

Question 72

In the molecular orbital model of the cyclopentadienyl cation,how many non-bonding molecular orbitals are there?

A)1
B)2
C)3
D)4
E)0

Question 73

In the molecular orbital model of the cyclopentadienyl cation,how many $\pi$ -antibonding molecular orbitals are there?

A)6
B)5
C)4
D)3
E)2

Question 74

In the molecular orbital model of cycloheptadienyl cation,how many pi electrons are in bonding molecular orbitals?

A)6
B)5
C)4
D)3
E)2

Question 75

In the molecular orbital model of cyclobutadiene,how many $\pi$ -antibonding molecular orbitals are there?

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

Question 76

In the molecular orbital model of the cyclopentadienyl cation,how many $\pi$ -bonding molecular orbitals are there?

A)6
B)5
C)4
D)3
E)2

Question 77

In the molecular orbital model of benzene,how many non-bonding molecular orbitals are there?

A)1
B)2
C)3
D)4
E)0

Question 78

In the molecular orbital model of cyclobutadiene,how many pairs of degenerate $\pi$ -molecular orbitals are there?

A)0
B)1
C)2
D)3
E)4

Question 79

In the molecular orbital model of cyclopentadienyl anion,how many pi electrons are in bonding molecular orbitals?

A)6
B)5
C)4
D)3
E)2

Question 80

In the molecular orbital model of cyclobutadiene,how many pairs of degenerate $\pi$ -antibonding molecular orbitals are there?

A)1
B)2
C)3
D)4
E)0