Deck 16: Electrophilic Attack on Derivatives of Benzene: Substituents Control Regioselectivity

Question 1

Which of the following resonance structures is the most stable?

A)

B)

C)

D)

E)

Answer 1

Question 2

Which of the following sequences of reactants would you expect to convert benzene to the substituted aromatic shown below?

A)

B)

C)

D) both A and B
E) both B and C

Answer 2

Question 3

Predict the major organic product of the following reaction.

A)

B)

C)

D)

E)

Answer 3

Question 4

What major product(s)would you expect from the following reaction?

A)

B)

C)

D)

E) both A and C

Question 5

What major product would you expect from the following reaction?

A)

B)

C)

D)

E)

Question 6

The explosive TNT is an isomer of trinitrotoluene.Given what you know about electrophilic aromatic substitution,which isomer is it most likely to be?

A)

B)

C)

D)

E)

Question 7

Rank the following aromatics in order of decreasing reactivity toward electrophilic aromatic substitution (most reactive > least reactive).

A) A > C > D > B
B) D > C > A > B
C) B > C > A > D
D) D > A > C > B
E) C > A > D > B

Question 8

What significant product(s)would not be formed in the following reaction?

A)

B)

C)

D) Neither A nor B would be formed.
E) Neither A nor C would be formed.

Question 9

In which electrophilic aromatic substitution reaction can unintended poly-substitution (i.e.,disubstitution,trisubstitution,etc.)be a problem?

A) Nitration
B) Friedel-Crafts acylation
C) Bromination
D) Friedel-Crafts alkylation
E) Chlorination

Question 10

What major product(s)would you expect from the reaction shown?

A)

B)

C)

D)

E) both A and C

Question 11

What would be the best way to prepare the ketone shown below?

A)

B)

C)

D) Any of these would work.
E) None of these would work.

Question 12

One of the interesting aspects of azulenes is that they are soluble in strong aqueous acids because of a reaction with H⁺.Which of the structures below would represent the most stable form of protonated azulene?

A)

B)

C)

D)

E)

Question 13

What product(s)would you expect from the following reaction?

A)

B)

C)

D)

E) both B and D

Question 14

Carefully consider the effect of the nitro groups on the stability of the intermediates involved as you decide which product(s)the reaction shown provides.

A)

B)

C)

D) both A and C
E) None of these would be formed.

Question 15

What major product(s)would you expect from the following reaction?

A)

B)

C)

D) both A and C
E) No reaction occurs.

Question 16

What major product(s)would you expect from the following reaction?

A)

B)

C)

D)

E) both A and C

Question 17

Which of the following statements is not true of the process shown below?

A) Benzene is less reactive with E⁺ than other alkenes are.
B) The overall process is a substitution reaction.
C) There are three resonance structures of the intermediate possible.
D) The first step is rate determining.
E) None of the above.All these statements are true.

Question 18

Rank the following in order of decreasing reactivity toward nitration (more reactive > less reactive).

A) D > C > B > A
B) B > D > C > A
C) D > B > C > A
D) C > D > B > A
E) A > C > D > B

Question 19

What reagent(s)would be required to accomplish the following reaction?

A) CH₃CH₂C(=O)Cl,AlCl₃
B) CH₃CH₂CH₂Cl,AlCl₃
C) Reagents in A,followed by HCl,Zn(Hg), $\Delta$
D) Reagents in B followed by zinc and HCl
E) CH₃CH=CH₂,H₂SO₄

Question 20

What would be the proper name of the molecule below?

A) benzotoluene
B) 3-methylnapthalene
C) 3-methyldibenzene
D) 2-methylnapthalene
E) 1-methylnapthalene

Question 21

Choose the appropriate reagents necessary to achieve this reaction:

A)

B) Zn(Hg).HCl, $\Delta$
C) Fe,HCl
D) CrO₃,H⁺,H₂O
E) None of these are appropriate reagents.

Question 22

Predict the product of the following reaction:

A)

B)

C)

D)

E) None of these are products.

Question 23

How many lines would be seen in the ¹³C NMR spectrum of the product from the following reaction?

A) 2
B) 3
C) 4
D) 5
E) 6

Question 24

Which of the following aromatics could you expect to make from benzene in the highest yield?

A)

B)

C)

D)

E)

Question 25

Considering the intermediate formed upon addition of an electrophile to this aromatic ring,which of the following is not a correct resonance structure:

A)

B)

C)

D)

E) All of these are correct.

Question 26

What would be the major product from the following reaction?

A)

B)

C)

D)

E) both A and C

Question 27

What would be the major product from the following reaction sequence?

A)

B)

C)

D)

E)

Question 28

Predict the major product of the following reaction:

A)

B)

C)

D)

E) None of these are products.

Question 29

Which of the following are not electron-withdrawing groups?

A) Carbonyl
B) Cyano
C) Alkyl
D) Sulfonyl
E) Nitro

Question 30

Rank the following in order of increasing reactivity toward electrophilic substitution:

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