Deck 17: Aromatic Compounds

Question 1

What is the IUPAC name for the following compound?

A) 5-bromophenol
B) 3-bromophenol
C) 5-bromoaniline
D) 3-bromoaniline
E) 1-bromophenol

Answer 1

3-bromophenol

Question 2

Give the common name for o-xylene.

A) hydroxybenzene
B) aminobenzene
C) 1,2-dimethylbenzene
D) ethylbenzene
E) 1,3-dimethylbenzene

Answer 2

1,2-dimethylbenzene

Question 3

Which of the following is another name for 4-chlorobenzaldehyde?

A) o-chlorobenzaldehyde
B) m-chlorobenzaldehyde
C) p-chlorobenzaldehyde
D) styrene
E) 1-chlorobenzaldehyde

Answer 3

p-chlorobenzaldehyde

Question 4

Identify the functional group in acetophenone.

A) ether
B) alkene
C) carboxylic acid
D) aldehyde
E) ketone

Question 5

What is the correct structure for 4-amino-2-chlorophenol?

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

Question 6

What is the IUPAC name for the following compound?

A) 6-ethyl-3-nitrobenzoic acid
B) 1-ethyl-4-nitrobenzoic acid
C) 2-ethyl-5-nitrobenzoic acid
D) 2-ethyl-5-nitrobenzaldehyde
E) 4-nitro-3-carboxyethylbenzene

Question 7

What is the IUPAC name for the following compound?

A) 4-butylphenol
B) 1-sec-butylphenol
C) 4-propylphenol
D) 4-sec-butylphenol
E) 1-isobutylphenol

Question 8

Give the common name for anisole.

A) hydroxybenzene
B) aminobenzene
C) methylbenzene
D) ethylbenzene
E) methoxybenzene

Question 9

What is the structure for 1,3-diphenylbutane?

Question 10

When the benzene ring is treated as a substituent, it is called a _________ group

Question 11

For disubstituted benzene derivatives, the descriptors ortho, meta, para are used when the parent is usually a ________.

Question 12

Give the common name for phenol.

A) hydroxybenzene
B) aminobenzene
C) methylbenzene
D) ethylbenzene
E) methoxybenzene

Question 13

What is the correct order of the names for the following compound?

A) I-naphthalene; II-triphenyl; III-biphenyl
B) I-naphthalene; II-phenanthrene; III-biphenyl
C) I-biphenyl; II-anthracene; III-naphthalene
D) I-naphthalene; II-anthracene; III-biphenyl
E) I-biphenyl; II- phenanthrene; III-naphthalene

Question 14

Identify the functional group in styrene.

A) ether
B) alkene
C) carboxylic acid
D) aldehyde
E) ketone

Question 15

What is the common name for the following compound?

Question 16

What is the IUPAC name for the following compound?

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

Question 17

What is the structure for p-aminobenzoic acid (PABA)?

Question 18

What is the structure for 4-amino-2-bromophenol?

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

Question 19

Give the common name for toluene.

A) hydroxybenzene
B) aminobenzene
C) methylbenzene
D) ethylbenzene
E) methoxybenzene

Question 20

What is the IUPAC name for the following compound?

A) 5-bromo-4-nitroaniline
B) 5-bromo-p-nitroaniline
C) 1-bromo-2-nitroaniline
D) 3-bromo-4-nitroaniline
E) p-nitro-m-bromoaniline

Question 21

Using a Frost circle, draw the molecular orbital energy diagram for the cyclopropenyl anion and predict if it is aromatic.

Question 22

For a compound to be aromatic, it must have a planar cyclic conjugated $\pi$ system along with an _____ number of electron pairs.

A) even
B) odd
C) either even or odd
D) none of these

Question 23

What is the IUPAC name for the following compound?

Question 24

What is the structure for styrene?

Question 25

The carbon-carbon bonds in benzene are _________.

A) of equal length and are shorter than the double bond
B) of equal length and are midway between a single bond and a double bond
C) of equal length and are longer than the single bond
D) of unequal length and alternate as single and double bonds
E) none of these

Question 26

Which of the following describes the current view of the two Kekulé structures for benzene?

A) they are both correct structures for benzene
B) the two structures are in equilibrium
C) the two structures adequately describe benzene
D) benzene is a resonance hybrid of the two structures
E) None of the above

Question 27

Which one of the following statements is not true for a compound to be considered as aromatic?

A) The compound must be cyclic and planar
B) The compound must be monocyclic.
C) The compound must have a conjugated system with a p orbital at every vertex
D) The compound must satisfy Hückel's rule -must have (4n + 2) $\pi$ electrons.
E) none of these

Question 28

The difference between the amount of heat actually released upon the hydrogenation of benzene and that calculated for the hydrogenation of an imaginary cyclohexatriene is called the ____ of benzene.

Question 29

According to molecular orbital theory, how many non-bonding molecular orbitals does benzene have?

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

Question 30

What is the IUPAC name for the following compound?

Question 31

According to molecular orbital theory, how many $\pi$ -bonding molecular orbitals does benzene have?

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

Question 32

Identify the number of $\pi$ electrons present in an aromatic compound.

A) 4n + 2
B) 2n + 2
C) 4n
D) 2n
E) 3n

Question 33

According to molecular orbital theory, how many $\pi$ -antibonding molecular orbitals does benzene have?

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

Question 34

What is the structure for 3-isobutyl-5-isopropylaniline?

Question 35

What is the main difference between an aromatic and antiaromatic compound?

A) Aromatic compounds must be cyclic and planar, but not antiaromatic compounds
B) Aromatic compounds must be monocyclic.
C) Antiaromatic compounds must have a conjugated system with a p orbital at every vertex
D) Aromatic compounds must satisfy Hückel's rule.
E) none of these

Question 36

Identify the number of $\pi$ electrons present in an antiaromatic compound.

A) 4n + 2
B) 2n + 2
C) 4n
D) none
E) none of these

Question 37

What is the IUPAC name for the following compound?

Question 38

Molecular orbitals of equal energy are referred to as _________ orbitals.

Question 39

According to the molecular orbital theory how many molecular orbitals are formed when the six p-orbitals of benzene combine?

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

Question 40

Identify the scientist credited with proposing the structure of benzene.

Question 41

Identify the structure that is an annulene.

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

Question 42

Which one of the following compounds is aromatic?

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

Question 43

Using a Frost circle, draw the molecular orbital energy diagram for the cyclononatetraenyl cation and predict if it is aromatic.

Question 44

Which one of the following compounds is antiaromatic?

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

Question 45

Which one of the following compounds is nonaromatic?

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

Question 46

Using a Frost circle, draw the molecular orbital energy diagram for the tropylium cation and predict if it is aromatic.

Question 47

Which one of the following compounds is aromatic?

A) I
B) II
C) III
D) IV
E) None of these

Question 48

Which one of the following compounds is antiaromatic?

A) I
B) II
C) III
D) IV
E) none of these

Question 49

Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.

Question 50

Which one of the following compounds is nonaromatic?

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

Question 51

Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.

Question 52

Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.

Question 53

Identify the structure that is not an annulene.

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

Question 54

Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.

Question 55

Which one of the following compounds is antiaromatic?

A) I
B) II
C) III
D) IV
E) none of these

Question 56

Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.

Question 57

Using a Frost circle, draw the molecular orbital energy diagram for the cyclopentadienyl anion and predict if it is aromatic.

Question 58

Which one of the following compounds is aromatic?

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

Question 59

Which one of the following compounds is aromatic?

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

Question 60

Which of the following annulenes is not aromatic?

A) [6]-annulene
B) [14]-annulene
C) [16]-annulene
D) [18]-annulene
E) [22]-annulene

Question 61

Identify the aromatic hydrocarbon with the highest stabilization energy per ring.

A) phenanthrene
B) benzene
C) naphthalene
D) anthracene

Question 62

Which one of the following compounds will undergo the fastest S_N1 reaction? Explain your choice.

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

Question 63

Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.

Question 64

Provide the product for the following reaction.

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

Question 65

Provide the reagent(s) necessary to convert toluene to benzoic acid.

A) Na₂Cr₂O₇/H₂SO₄/H₂O
B) 1. NBS, $\Delta$ 2.NaOH
C) 1. LiAlH₄ 2. H₃O⁺
D) H₂, Pd
E) 1. CO_2, 2. H₃O⁺

Question 66

Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.

Question 67

Provide the product for the following reaction. Explain your answer.

Question 68

Both pyridine and pyrrole are nitrogen containing aromatic heterocyclic compounds. When treated with HCl, only pyridine forms the hydrochloride salt, whereas pyrrole is unreactive. Provide an explanation for this observed reactivity.

Question 69

Which one of the following compounds is most acidic? Explain your choice.

Question 70

Which one of the following compounds will undergo the fastest S_N1 reaction? Explain your choice.

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

Question 71

Which of the following compounds is most acidic?

A) I
B) II
C) III
D) both I and II
E) both II and III

Question 72

Classify the following compounds as aromatic, antiaromatic, or nonaromatic. Explain your choice.

Question 73

Which one of the following compounds is most acidic?

A) I
B) II
C) III
D) IV
E) none of these

Question 74

Identify the aromatic hydrocarbon with the highest stabilization energy.

A) phenanthrene
B) benzene
C) naphthalene
D) anthracene

Question 75

Classify the following compounds as aromatic, antiaromatic, or nonaromatic. Explain your choice.

Question 76

Provide the structure of the major product(s) for the following reaction.

A) I
B) II
C) III
D) IV
E) Both I and II

Question 77

The pK_a of cyclopentadiene (I) and cycloheptatriene (II) is around 16 and 36 respectively. Explain the difference in the two pK_a values.

Question 78

Which one of the following compounds is most acidic?

A) I
B) II
C) III
D) I & III
E) II & III

Question 79

Classify the following compound as aromatic, antiaromatic, or nonaromatic. Explain your choice.

Question 80

Provide the product for the following reaction.

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