Deck 18: Aromatic Compounds

Question 1

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 1

p-chlorobenzaldehyde

Question 2

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

Answer 2

3-bromo-4-nitroaniline

Question 3

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

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

Answer 3

II

Question 4

o-xylene is the common name for:

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

Question 5

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

Question 6

What is the IUPAC name for the following compound?

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

Question 7

What is the IUPAC name for the following compound?

Question 8

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

Question 9

Anisole is the common name for:

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

Question 10

What is the structure for 1,3-diphenylbutane?

Question 11

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

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

Question 12

Toluene is the common name for:

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

Question 13

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 14

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 15

What is the common name for the following compound?

Question 16

Phenol is the common name for:

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

Question 17

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 18

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 19

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

Question 20

What is the IUPAC name for the following compound?

Question 21

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

Question 22

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

Question 23

What is the IUPAC name for the following compound?

Question 24

According to molecular orbital theory, how many $\pi$ -antibonding molecular orbitals are there for benzene?

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

Question 25

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 describes benzene;
D) benzene is a resonance hybrid of the two structures
E) None of the above

Question 26

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 p orbital at every vertex
D) Aromatic compounds must satisfy Hückel's rule.
E) none of these

Question 27

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

Question 28

The number of π electrons present in an antiaromatic compound:

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

Question 29

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
D) of unequal length and alternate as single and double bond
E) none of these

Question 30

The number of π electrons present in an aromatic compound:

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

Question 31

What is the structure for styrene?

Question 32

According to molecular orbital theory, how many non-bonding molecular orbitals are there for benzene?

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

Question 33

According to molecular orbital theory, how many $\pi$ -bonding molecular orbitals are there for benzene?

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

Question 34

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

Question 35

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

Question 36

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

Question 37

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

Question 38

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 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

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 p orbital at every vertex
D) The compound must satisfy Hückel's rule -must have (4n + 2) $\pi$ electrons.
E) none of these

Question 41

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

Question 42

Which one of the following compound is antiaromatic?

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

Question 43

Which one of the following compound is nonaromatic?

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

Question 44

Which one of the following compound is nonaromatic?

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

Question 45

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

Question 46

Which one of the following compound is aromatic?

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

Question 47

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

Question 48

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

Question 49

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

Question 50

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

Question 51

Which one of the following compound is aromatic?

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

Question 52

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

Question 53

Which one of the following compounds is aromatic?

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

Question 54

Which one of the following compounds is antiaromatic?

Question 55

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

Question 56

Which one of the following compound is aromatic?

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

Question 57

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

Question 58

Which of the following annulenes is not aromatic?

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

Question 59

Which one of the following compound(s) is antiaromatic?

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

Question 60

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

Question 61

Provide the structures of the intermediate and final products in the following reaction sequence.

Question 62

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

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

Question 63

Provide the reagents necessary to carry out the following conversion.

Question 64

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 65

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

Question 66

Provide the product for the following reaction?

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

Question 67

Provide the reagents necessary to convert ethylbenzene to styrene.

Question 68

Provide the product for the following reaction?

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

Question 69

Which one of the following compounds is most acidic?

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

Question 70

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

Question 71

Provide the reagents necessary to carry out the following conversion.

Question 72

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

Question 73

Which of the following compounds is most acidic?

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

Question 74

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

Question 75

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

Question 76

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

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

Question 77

Which one of the following compounds is most acidic?

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

Question 78

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

Question 79

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 80

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