Deck 18: Aromatic Compounds

Question 1

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

Answer 1

2-ethyl-5-nitrobenzoic acid

Question 2

Phenol is the common name for:

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

Answer 2

hydroxybenzene

Question 3

What is the IUPAC name for the following compound?

Answer 3

2-ethyl-4-fluoro-5-methylbenzaldehyde

Question 4

Anisole is the common name for:

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

Question 5

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 6

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

Question 7

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 8

What is the IUPAC name for the following compound?

Question 9

What is the structure of styrene?

Question 10

Toluene is the common name for:

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

Question 11

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 12

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

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

Question 13

What is the IUPAC name for the following compound?

Question 14

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 15

o-xylene is the common name for:

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

Question 16

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

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

Question 17

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

Question 18

What is the structure for 1,3-diphenylbutane?

Question 19

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 20

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

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

Question 21

Which one of the following compound is nonaromatic?

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

Question 22

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

Question 23

Which one of the following compound is nonaromatic?

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

Question 24

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

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

Question 25

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 26

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

Question 27

Which one of the following compounds is antiaromatic?

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

Question 28

Which one of the following statement 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 29

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

Question 30

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

Question 31

Which one of the following compound is antiaromatic?

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

Question 32

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

Question 33

Which one of the following compounds is aromatic?

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

Question 34

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 35

Which one of the following compound is aromatic?

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

Question 36

Which one of the following compound is aromatic?

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

Question 37

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

Question 38

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 39

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

Question 40

Which one of the following compound is aromatic?

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

Question 41

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

Question 42

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

Question 43

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

Question 44

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

Question 45

Provide the product for the following reaction?

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

Question 46

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

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

Question 47

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

Question 48

Provide the product for the following reaction?

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

Question 49

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

Question 50

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

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

Question 51

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

Question 52

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 53

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

Question 54

Which one of the following compounds is most acidic?

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

Question 55

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

Question 56

Which one of the following compounds is most acidic?

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

Question 57

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

Question 58

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

Question 59

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 60

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

Question 61

The three isomers of dimethylbenzene are commonly named o-xylene,m-xylene,
p-xylene.These three isomers are difficult to distinguish using ¹H NMR,but they can be easily identified using ¹³C NMR.Describe how ¹³C NMR distinguishes these three isomers.

Question 62

Provide a structure for the compound with molecular formula C₁₀H₁₂O₂ and with the following spectroscopic data.IR: 1680 cm⁻¹,2750 cm⁻¹,2850 cm^−1
1H NMR: 1.1 $\delta$ (triplet,I=3H),3.5 $\delta$ (quartet,I=2H),4.5 $\delta$ (singlet,I=2H),7.3 $\delta$ (doublet,I=2H),7.7 $\delta$ (doublet,I=2H),9.9 $\delta$ (singlet,I=1H)

Question 63

Provide a structure for the compound with molecular formula C₉H₁₂ and with the following spectroscopic data.
¹H NMR: 1.2 $\delta$ (doublet,I=6H),3.0 $\delta$ (septet,I=1H),7.1 $\delta$ (singlet,I=5H)

Question 64

Provide stepwise synthesis for the following

Question 65

Predict the product for the following reaction.

Question 66

Which of the following isomer(s)of tribromoaniline will show two doublets with 7.5 Hz coupling in ¹HNMR spectrum?

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

Question 67

Provide stepwise synthesis for the following

Question 68

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

Question 69

Provide a structure for the compound with molecular formula C₉H₉ClO and with the following spectroscopic data.
IR: 1680 cm^−1
1H NMR: 3.5 $\delta$ (triplet,I=2H),4.0 $\delta$ (triplet,I=2H),7.4 $\delta$ (triplet,I=2H),7.6 $\delta$ (doublet,I=1H),7.9 $\delta$ (triplet,I=2H)

Question 70

Provide the reagents necessary to carry out the following conversion.

Question 71

Provide the reagents necessary to carry out the following conversion.

Question 72

Predict the product for the following reaction.

Question 73

Which one of the following compounds would exhibit seven signals in its ¹³C NMR spectrum?

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

Question 74

Provide the structure(s)of the intermediate product(s)in the following reaction sequence.

Question 75

Predict the product for the following reaction.

Question 76

Predict the product for the following reaction.

Question 77

Provide the reagents necessary to carry out the following conversion.

Question 78

Provide stepwise synthesis for the following

Question 79

Provide the reagents necessary to convert ethylbenzene to styrene.