Deck 19: Aromatic Substitution Reactions

Question 1

Provide all the resonance structures of the sigma complex,when benzene reacts with an electrophile (E⁺).

Answer 1

Question 2

The electrophile in the nitration reaction of benzene is:

A)NO₂⁺
B)HNO₃
C)NO₃⁺
D)H₂SO₄
E)NO₂

Answer 2

NO₂⁺

Question 3

Predict the major product for the following reaction.

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

Answer 3

III

Question 4

Predict the major product for the reaction between benzene and 2-chlorobutane in the presence of AlCl₃.

A)Chlorobenzene
B)sec-butylbenzene
C)ethylbenzene
D)isopropylbenzene
E)t-butylbenzene

Question 5

Predict the major product for the following reaction.

Question 6

Which of these is the rate-determining step in the electrophilic aromatic substitution of benzene?

A)Formation of an electrophile
B)Formation of sigma complex.
C)Loss of proton from sigma complex.
D)Addition of electrophile & loss of proton
E)None of these

Question 7

Predict the major product for the following reaction.

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

Question 8

Predict the major product for the following reaction.

Question 9

Which one of the following reactions is most likely to give a polysubstituted product?

A)Friedel-Crafts alkylation
B)Friedel-Crafts acylation
C)Nitration
D)Sulfonation
E)Halogenation

Question 10

Provide a stepwise curved arrow mechanism for chlorination of benzene in the presence of FeCl₃.

Question 11

The electrophile in the sulfonation reaction of benzene is:

A)SO₂⁺
B)H₂SO₄
C)SO₃⁺
D)H₂SO₃
E)SO₃

Question 12

Predict the product for the following reaction.

Question 13

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

Question 14

Which chemical test would you use to distinguish between ethylbenzene and styrene?

Question 15

Which one of the following compounds does not undergo Friedel-Crafts reaction?

A)Benzene
B)Chlorobenzene
C)Nitrobenzene
D)Toluene
E) $\underline{\text{ tert }}$ -Butylbenzene

Question 16

Provide a stepwise curved arrow mechanism for the following reaction.

Question 17

Predict the product for the following reaction.

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

Question 18

Predict the product for the following reaction.

Question 19

Cyclohexene undergoes addition reaction with bromine,but benzene does not.Instead benzene undergoes a substitution reaction with bromine.Explain.

Question 20

Predict the major product for the following reaction.

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

Question 21

Predict the structure of the major product for the following reaction.

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

Question 22

Predict the structure of the product for the following reaction.

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

Question 23

Predict the major product for the following reaction.

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

Question 24

Predict the structure of the major product for the following reaction.

Question 25

Predict the major product for the following reaction and provide a stepwise curved arrow mechanism for the formation of the product.

Question 26

Predict the major product for the following reaction.

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

Question 27

Provide all resonance structures of the sigma complex when aniline reacts with an electrophile (E⁺)to yield the para-substituted product.

Question 28

Which one of the following compounds would be least reactive toward electrophilic aromatic substitution?

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

Question 29

Predict the major product for the following reaction.

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

Question 30

Predict the major product for the following reaction.

Question 31

Arrange the following compounds in order of decreasing reactivity towards electrophilic aromatic substitution:

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

Question 32

Predict the structure of the product for the following reaction.

Question 33

Provide the reagent(s)that are necessary to carry out the following conversion.t-butylbenzene $\rightarrow$ 4-chloro-1-t-butylbenzene

A)Cl₂,heat
B)Cl₂,FeCl₃
C)SOCl₂,pyridine
D)HCl
E)PCl₃

Question 34

Provide the structure of the major products formed in the following reaction sequence.

Question 35

Which one of the following compounds would be most reactive toward electrophilic aromatic substitution?

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

Question 36

Predict the structure of the product for the following reaction.

Question 37

Predict the structure of the major product for the following reaction.

Question 38

Which one of the following compounds will be most reactive towards bromination reaction?

A)nitrobenzene
B)anisole
C)acetanilide
D)benzene
E)benzaldehyde

Question 39

Predict the structure of the major product for the following reaction.

Question 40

Predict the major product for the following reaction.

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

Question 41

Predict the major product for the following reaction.

Question 42

Predict the major product for the following reaction.

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

Question 43

Predict the product for the following reaction.

Question 44

Predict the product for the following reaction.

Question 45

Predict the major product for the following reaction.

Question 46

Predict the major product for the following reaction.

Question 47

Provide the reagents necessary to carry out the following conversion.

Question 48

Predict the product for the following reaction.

Question 49

Starting with benzene propose a stepwise synthesis for the following compound.

Question 50

Predict the major product for the following reaction.

Question 51

Predict the product for the following reaction.

Question 52

Predict the product(s)for the following reaction.

Question 53

Predict the major product for the following reaction.

Question 54

Predict the major product for the following reaction.

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

Question 55

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

Question 56

Predict the product(s)for the following reaction.

Question 57

Predict the major product for the following reaction.

A)I
B)II
C)III
D)IV
E)no reaction

Question 58

Predict the major product for the following reaction.

A)I
B)II
C)III
D)IV
E)no reaction

Question 59

Predict the major product for the following reaction.

Question 60

Predict the major product for the following reaction.

Question 61

Draw the major resonance contributors for the intermediate that results when p-nitrochlorobenzene is treated with NaOH.

Question 62

Provide the structures of major resonance contributors when nitrobenzene reacts with an electrophile in electrophilic aromatic substitution at the meta position.

Question 63

Starting with benzene propose a stepwise synthesis for the following compound.

Question 64

Predict the product and provide a stepwise curved arrow mechanism for the following reaction.