Deck 9: Benzene and Its Derivatives

Question 1

Substitution of a bromine atom for a hydrogen atom in anthracene leads to the formation of how many C₁₄H₉Br isomers?

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

Answer 1

3

Question 2

Which of the following are intermediates in the mechanism of the reaction of phenol and acetone in the presence of phosphoric acid (a strong mineral acid)?

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

Answer 2

I and IV

Question 3

What is the major contributing structure to the cation intermediate of the bromination of anisole?

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

Answer 3

IV

Question 4

Which is the electrophile in the following reaction?

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

Question 5

How many Kekule structures are possible for benzene, naphthalene, and anthracene ?

A) I: 3, II: 4, III: 4
B) I: 2, II: 3, III: 4
C) I: 2, II: 4, III: 4
D) I: 3, II: 3, III: 4

Question 6

Which is the major product of the following reactions?

A) para-chlorobenzoic acid
B) meta-chlorobenzoic acid
C) a mixture of para- and meta-chlorobenzoic acid
D) a mixture of ortho- and para-chlorobenzoic acid

Question 7

How many $\pi$ -orbital electrons are in the following molecules?

A) imidazole: 5, adenine: 10, caffeine: 5
B) imidazole: 6, adenine: 9, caffeine: 6
C) imidazole: 6, adenine: 10, caffeine: 6
D) imidazole; 4, adenine, 9, caffeine, 5

Question 8

Which structures are aromatic? Make your call based on the electron distributions shown here, not on possible resonance structures.

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

Question 9

Arrange the compounds in order of decreasing reactivity towards the aromatic nitration reaction.

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

Question 10

Which is the electrophile in the nitration of benzene?

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

Question 11

Substitution of a bromine atom for a hydrogen atom in naphthalene leads to the formation of how many C₁₀H₇Br isomers?

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

Question 12

Which is the major product of the following reaction?

A) 1-chloro-4-nitrobenzene
B) 1-chloro-3-nitrobenzene
C) 1-chloro-2-nitrobenzene
D) a mixture of 1-chloro-4-nitrobenzene and 1-chloro-2-nitrobenzene

Question 13

Which are the final reaction products (2), which are formed by the following sequence of reactions.?

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

Question 14

Which of the named compounds have correct structures?

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

Question 15

Which are the major reaction products of the following reaction, which is carried out in an inert solvent?

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

Question 16

Arrange the compounds in order of increasing reactivity toward electrophilic aromatic substitution (lowest first).

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

Question 17

Arrange the compounds in order of increasing reactivity toward electrophilic aromatic substitution (lowest first).

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

Question 18

Which are the major reaction products of the following reaction, which is carried out in an inert solvent?

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

Question 19

Which structures have the correct IUPAC names?

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

Question 20

Substitution of a bromine atom for a hydrogen atom in benzene leads to the formation of how many different C₆H₅Br isomers?

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

Question 21

The reagent that completes the following reaction is

Question 22

When one mole of sodium hydroxide is allowed to react with a mixture of one mole of phenol and one mole of cyclohexanol, the major organic products are?

Question 23

The name of the following structure is 2,4-diethylnitrobenzene.

Question 24

The name of the following structure is 3,5-dibromobenzoic acid.

Question 25

Which is the best reaction sequence for preparing the following compound from benzene?

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

Question 26

Which is the best reaction sequence for preparing the following compound from benzene? (HINT: consider only the reaction product from electrophilic addition in the ortho position).

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

Question 27

Which is the major product from the following consecutive reactions?

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

Question 28

The two major products of the following reaction are?

Question 29

The major product of the following reaction is,

Question 30

The reaction arrows (curved arrows) required to complete the following reaction mechanisms are,

Question 31

Your choice of starting material and reagent that complete the following reaction are?

Question 32

Your choice of starting material, intermediate and reagents that complete the following reaction are?

Question 33

Arrange the compounds in order of increasing acidity (least first).

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

Question 34

The two major products of the following reaction are ?

Question 35

When one mole of sodium bicarbonate is allowed to react with a mixture of one mole of benzoic acid and one mole of phenol, the major organic products are?

Question 36

Which is the product in the following reaction?

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

Question 37

Arrange the compounds in order of increasing acidity (least first).

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

Question 38

Which is the major product of the following reaction?

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

Question 39

Arrange the compounds in order of increasing acidity (least first).

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

Question 40

Which of the following properties would allow a student to decide whether an unknown compound was more likely to be para-cresol (para-methylphenol) or benzyl alcohol?

A) solubility in water
B) solubility in aqueous hydrochloric acid solution
C) solubility in aqueous sodium bicarbonate solution
D) solubility in aqueous sodium hydroxide solution

Question 41

The following compounds are listed in decreasing order of reactivity toward electrophilic aromatic substitution.

Question 42

The following compound is aromatic.

Question 43

The following reaction scheme will synthesize the product shown.

Question 44

The product of the reaction of toluene with concentrated nitric and sulfuric acid is m-nitrotoluene.

Question 45

The following reaction scheme will synthesize the product shown.

Question 46

The following compounds are listed in decreasing order of reactivity toward electrophilic aromatic substitution.

Question 47

The product of the reaction of isopropylbenzene with chromic acid is methylphenyl ketone.

Question 48

The following ion is aromatic.