Deck 25: Electrophilic Aromatic Substitution 2: Substitution on Mono- and Disubstituted Benzene and Other Aromatic Rings

Question 1

Which of the following would undergo nitration at the highest rate?

A)
B)
C)
D)
E)

Answer 1

Question 2

Which of the following resonance structures is least stable?

A)
B)
C)
D)
E)

Answer 2

Question 3

Which of the following is an intermediate in the mechanism for the reaction below?

A)
B)
C)
D)
E)

Answer 3

Question 4

Which of the following statements is true regarding the two reactions shown below?

A)Both reactions will occur at a slower rate than the nitration of benzene, and both will yield the meta-substituted product.
B)Both reactions will occur at a faster rate than the nitration of benzene. Reaction I will yield ortho/para-substituted products, and Reaction II will yield the meta-substituted product.
C)Both reactions will yield meta-substituted products. Reaction I will be slower than the nitration of benzene, while Reaction II will be faster.
D)Both reactions will yield ortho/para-substituted products. Reaction I will be faster than the nitration of benzene, while Reaction II will be slower.
E)Both reactions will occur at a slower rate than the nitration of benzene. Reaction I will yield the meta-substituted product, and Reaction II will yield ortho/para-substituted products.

Question 5

Which sequence of reactions would be the best choice to carry out the step below?

A)
B)
C)
D)
E)

Question 6

Which of the following would produce a mixture of two isomers as the major products when allowed to react with Cl₂ and AlCl₃?

A)
B)
C)
D)
E)

Question 7

Which of the following substituents is an activating group?

A)
B)
C)
D)
E)

Question 8

Which of the following substituents is an ortho/para-directing group?

A)
B)
C)
D)
E)

Question 9

How many of the following molecules will undergo chlorination at a higher rate than benzene and will produce ortho/para-substituted products?

A)One
B)Two
C)Three
D)Four
E)Five

Question 10

Which structure represents a major intermediate in the chlorination of nitrobenzene?

A)
B)
C)
D)
E)

Question 11

Which of the following correctly explains why alkyl groups are ortho/para-directing groups?

A)Meta substitution results in an arenium ion in which a positive charge is destabilized by an adjacent electron-withdrawing group.
B)Ortho/para substitution results in an arenium ion intermediate in which all atoms have complete octets.
C)A lone pair of electrons on the alkyl group participates in resonance and stabilizes the arenium ion intermediate in ortho/para substitution.
D)The most stable resonance structure for the arenium ion intermediate in ortho/para substitution contains a 2° carbocation.
E)The alkyl group is electron donating via induction and stabilizes the adjacent positive charge in the ortho/para substitution intermediate.

Question 12

Which of the following substituents is an activating ortho/para-directing group?

A)
B)
C)
D)
E)

Question 13

How many isomeric products could result from the reaction below?

A)One
B)Two
C)Three
D)Four
E)Five

Question 14

Predict the major product of the following reaction.

A)
B)
C)
D)
E)

Question 15

In which of the following arenium ions do all atoms have a complete octet?

A)
B)
C)
D)
E)

Question 16

Which of the following is the correct order of increasing rate of bromination for the three molecules below?

A)2 < 3 < 1
B)1 < 2 < 3
C)2 < 1 < 3
D)3 < 2 < 1
E)3 < 1 < 2

Question 17

Predict the major product of the following reaction.

A)
B)
C)
D)
E)

Question 18

Which of the following arenium ions is most stable?

A)
B)
C)
D)
E)

Question 19

Rank the following from slowest to fastest rate of nitration.

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

Question 20

Which of the following could undergo a nucleophilic aromatic substitution via addition-elimination?

A)
B)
C)
D)
E)

Question 21

What arenium intermediates are formed in the ortho- and meta-substituted products of the reaction below? Draw a mechanism that leads to the formation of each intermediate,and use resonance structures to explain which would be the major product.

Question 22

Draw a complete,detailed mechanism for the reaction below.Label each elementary step,and indicate the rate-determining step.

Question 23

Fill in the missing reagents to carry out the synthesis below.

A)
B)HNO₃, H₂SO₄
C)
D)ZN(Hg), HCl
E)KMnO₄, NaOH, 

Question 24

Rank the following intermediates from highest to lowest potential energy.

Question 25

Draw a complete,detailed mechanism for the reaction below.Also draw a resonance structure that shows why the methoxy group is an ortho/para-directing group.

Question 26

Halogen substituents are deactivating but are ortho/para directors.Explain.

Question 27

Predict the major product of the reaction below.

Question 28

Draw the most stable resonance structure of the intermediate formed in the reaction below,and predict the major product(s).

Question 29

Predict the two major products of the reaction below.

Question 30

Which of the following would be a major product of the reaction below?

A)
B)
C)
D)
E)

Question 31

Predict the major product of the following reaction sequence.

A)
B)
C)
D)
E)

Question 32

Predict the major product of the reaction below.

Question 33

Fill in the necessary reagent and solvent to carry out the reaction below.

Question 34

Give an example of a monosubstituted benzene ring that would undergo bromination at a higher rate than toluene.

Question 35

A student proposes the following synthesis to produce ethylbenzene as the major product.Explain the error in this proposed synthesis,and suggest an alternative synthetic route.

Question 36

Draw a resonance structure to explain why anisole undergoes electrophilic aromatic nitration reactions at a higher rate than benzene.

Question 37

Predict the major product of the following reaction sequence.

A)
B)
C)
D)
E)

Question 38

Briefly explain why the reaction below would be unsuccessful.

Question 39

What is the major product of the following sequence of reactions?

A)
B)
C)
D)
E)

Question 40

Predict the major product(s)of the reaction below,and draw three resonance structures for the intermediate that is formed.

Question 41

Draw the mechanism for the reaction below.Label each elementary step.

Question 42

An amine substituent will coordinate to a Lewis acid such as AlCl₃,thereby deactivating the benzene ring.If the amine is converted to an amide,however,this coordination does not take place.Briefly explain why this is so,using a resonance structure to illustrate your answer.

Question 43

Draw all possible isomers that could be formed in the reaction below,and predict the major product.

Question 44

Draw a complete,detailed mechanism for the reaction below,and predict the product.Draw the structure of the most stable intermediate.

Question 45

Show how you would synthesize the compound below from benzene.

Question 46

Draw the mechanism for the reaction below,including the structure of the most stable intermediate,and predict the major product.Label each step,and indicate the rate-determining step.

Question 47

Arrange the following in order of increasing reaction rate with respect to nucleophilic aromatic substitution by methylamine.

Question 48

Devise a synthesis to carry out the following transformation.

Question 49

Fill in the missing starting material for the synthesis below.

Question 50

Fill in the intermediates and reagents to complete the synthetic scheme below.