Deck 24: Electrophilic Aromatic Substitution 1: Substitution on Benzene; Useful Accompanying Reactions

Question 1

What is the expected product for the following reaction?

A)I
B)II
C)III
D)IV
E)None of these will be produced.

Answer 1

III

Question 2

Which mechanism step is not found in the nitration of benzene?

A)Coordination
B)Heterolysis
C)Electrophilic addition
D)Electrophile elimination
E)Proton transfer

Answer 2

Coordination

Question 3

Which of the following is not true of Friedel-Crafts acylation reactions?

A)They require an AlCl₃ catalyst.
B)They proceed through an acylium ion intermediate.
C)They are susceptible to carbocation rearrangements.
D)They require an acid halide as a starting material.
E)They create aromatic ketones.

Answer 3

They are susceptible to carbocation rearrangements.

Question 4

Which of the following is true regarding sulfonation?

A)Sulfonation can be used as a protecting group.
B)Sulfonation requires the nucleophilic addition of SO₃.
C)Sulfonation slows down with the addition of fuming sulfuric acid.
D)Sulfonation is irreversible.
E)Sulfonation requires nucleophile elimination in its mechanism.

Question 5

Which reagent(s)will complete the following reaction?

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

Question 6

What is the starting material that best completes the following reaction?

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

Question 7

Which reagent(s)will best complete the following reaction?

A)Cl₂
B)NaCl
C)HCl
D)Cl₂, FeCl₃
E)AlCl₃

Question 8

What is the product of the following reaction?

A)I
B)II
C)III
D)IV
E)No reaction will occur.

Question 9

What is the most likely product of the following reaction?

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

Question 10

What is the product of the following reaction?

A)I
B)II
C)III
D)IV
E)None of these is the product.

Question 11

Which reagent(s)will best complete the following reaction?

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

Question 12

Which of the following mechanism steps would be included in the following general mechanism?

A)Nucleophilic addition
B)Nucleophile elimination
C)S_N2
D)Electrophilic addition
E)Carbocation rearrangement

Question 13

What is the most likely product of the following reaction?

A)I
B)II
C)III
D)IV
E)No reaction will occur.

Question 14

Which reagent(s)will complete the following reaction?

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

Question 15

Which reagent(s)will best complete the following reaction?

A)I
B)II
C)III
D)IV
E)Both I and II will complete the reaction.

Question 16

What reagent(s)will complete the following reaction?

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

Question 17

Which of the following is not included in the mechanism for the following reaction?

A)Coordination
B)Electrophilic addition
C)Electrophile elimination
D)Nucleophile elimination
E)1,2-hydride shift

Question 18

Which reagent(s)will best complete the following reaction?

A)I
B)II
C)III
D)IV
E)Both I and II will complete the reaction.

Question 19

What is the most likely product of the following reaction?

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

Question 20

What is the product of the following reaction?

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

Question 21

Starting with the following,give the general mechanism for electrophilic addition.

Question 22

Which reagent(s)will best convert benzene into methyl benzoate?

A)I
B)II
C)III
D)IV
E)None of these will convert benzene to methyl benzoate.

Question 23

Give the product of the following reaction.

Question 24

Give the mechanism and product for the following reaction.

Question 25

What is the most likely product of the following reaction?

Question 26

Indicate what types of mechanism steps are involved in the following reaction sequence.

Question 27

Identify the reagents that best complete the following reaction.

Question 28

Give the mechanism for the creation of nitrosonium ion from concentrated nitric acid.

Question 29

What is the most likely product of the following set of reactions?

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

Question 30

Show how the following molecule can be synthesized from benzene.

Question 31

What is the most likely product of the following reaction?

Question 32

What is the most likely product of the following reaction?

Question 33

What is the most likely product of the following reaction?

A)I
B)II
C)III
D)IV
E)No reaction will occur.

Question 34

What is the most likely product of the following reaction?

Question 35

Show how the following molecule can be synthesized from benzene.

Question 36

Which of the following starting materials will not produce benzoic acid when treated with hot KMnO₄?

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

Question 37

Give the product of the following reaction.

Question 38

Explain why the following reaction does not occur.

Question 39

What reagents are required to complete the following reaction?

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

Question 40

Identify the reagents that best complete the following reaction.

Question 41

Show how the following compound can be synthesized from benzene.

Question 42

Show how aniline can be converted to benzene.

Question 43

Show how the following compound can be synthesized from benzene.

Question 44

What is the product of the following reaction?

Question 45

What is the product of the following set of reactions on benzene?

Question 46

What starting material is required for the following synthesis?

Question 47

Show how phenol can be synthesized from nitrobenzene.

Question 48

What is the product of the following reaction?

Question 49

What reagents best complete the following reaction?

Question 50

What is the product of the following reaction?