Question 1

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

Accepted Answer

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Question 2

Which of the following compounds undergoes reaction with HNO3/H2SO4 at the fastest rate?

Accepted Answer

A)   ethylbenzene
B)   benzenesulfonic acid
C)   nitrobenzene
D)   chlorobenzene
E)   acetophenone A

Question 3

Which of the following compounds will undergo bromination most rapidly using Br2, FeBr3?

Accepted Answer

A)   p-methylacetanilide
B)   bromobenzene
C)   acetanilide
D)   benzenesulfonic acid
E)   dibromobenzene A

Question 4

What type of reaction is shown below? (Org. Lett., 2013, 15 (15), 3950-3953)

Accepted Answer

A)   Heck reaction
B)   Suzuki coupling
C)   Organocuprate coupling
D)   Birch reduction

Question 5

Draw the major organic structure that results from the following sequence of reactions.

Accepted Answer

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Question 6

Provide the major organic product that results when benzene is treated with the following sequence of reagents: 1. HNO₃, H₂SO₄ 2. Br₂, FeBr₃.

Accepted Answer

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Question 7

Provide the major organic product(s) of the reaction shown below.

Accepted Answer

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Question 8

Draw the three major resonance structures of the sigma complex intermediate in the reaction of acetophenone with HNO₃/H₂SO₄ to yield o-nitroacetophenone. Circle the resonance form which is less stable than the other two.

Accepted Answer

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Question 9

Provide a series of synthetic steps by which 3-bromoethylbenzene can be prepared from benzene.

Accepted Answer

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Question 10

Provide a series of synthetic steps by which 2-bromo-4-nitrobenzoic acid can be prepared from toluene.

Accepted Answer

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Question 11

Which of the following compounds would most likely be used in the preparation of isobutylbenzene from benzene?

Accepted Answer

A)   (CH3) 2CHCOCl
B)   (CH3) 2CHCH2Cl
C)   (CH3) 2CHCH2Br
D)   CH3CH2CH2CH2Cl
E)   CH3CH2CH2COCl

Question 12

Provide the structure of the major monoitration product of the compound below.

Accepted Answer

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Question 13

Provide the major resonance structures of the intermediate sigma complex in the reaction of benzene with the generic electrophile E⁺.

Accepted Answer

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Question 14

Provide the major organic product of the following reaction sequence.

Accepted Answer

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Question 15

Provide the major organic product of the following reaction.

Accepted Answer

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Question 16

Provide the major organic product of the following reaction.

Accepted Answer

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Question 17

Name the major organic product which results when 3-ethylbenzenesulfonic acid is heated in aqueous acid.

Accepted Answer

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Question 18

In electrophilic aromatic substitution reactions the hydroxyl group is an o,p-director because ________.

Accepted Answer

A)   it donates electron density to the ring by induction and destabilizes the meta sigma complex
B)   it donates electron density to the ring by resonance and stabilizes the ortho and para sigma complexes
C)   it donates electron density to the ring by induction and stabilizes the ortho and para sigma complexes
D)   it donates electron density to the ring by resonance and destabilizes the meta sigma complex
E)   it withdraws electron density from the ring by induction and destabilizes the meta sigma complex

Question 19

When 2,4-dinitrochlorobenzene is treated with sodium hydroxide at 100°C followed by protonation ________.

Accepted Answer

A)   2,4-dinitrophenol is formed via an addition-elimination nucleophilic aromatic substitution mechanism
B)   2,4-dinitrophenol is formed via an elimination-addition nucleophilic aromatic substitution mechanism
C)   3,5-dinitrophenol is formed via an elimination-addition nucleophilic aromatic substitution mechanism
D)   3,5-dinitrophenol is formed via an electrophilic aromatic substitution mechanism
E)   2,4-dinitrophenol is formed via an electrophilic aromatic substitution mechanism

Question 20

Which of the following species is attacked by benzene in the electrophilic nitration reaction?

Accepted Answer

A)   HNO3
B)   NO2+
C)   NO2
D)   NO+
E)   N3-

Exam 17: Reactions of Aromatic Compounds

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

Which of the following compounds undergoes reaction with HNO₃/H₂SO₄ at the fastest rate?

Which of the following compounds will undergo bromination most rapidly using Br₂, FeBr₃?

What type of reaction is shown below? (Org. Lett., 2013, 15 (15) , 3950-3953)

Draw the major organic structure that results from the following sequence of reactions.

Provide the major organic product that results when benzene is treated with the following sequence of reagents: 1. HNO₃, H₂SO₄ 2. Br₂, FeBr₃.

Provide the major organic product(s) of the reaction shown below.

Draw the three major resonance structures of the sigma complex intermediate in the reaction of acetophenone with HNO₃/H₂SO₄ to yield o-nitroacetophenone. Circle the resonance form which is less stable than the other two.

Provide a series of synthetic steps by which 3-bromoethylbenzene can be prepared from benzene.

Provide a series of synthetic steps by which 2-bromo-4-nitrobenzoic acid can be prepared from toluene.

Which of the following compounds would most likely be used in the preparation of isobutylbenzene from benzene?

Provide the structure of the major monoitration product of the compound below.

Provide the major resonance structures of the intermediate sigma complex in the reaction of benzene with the generic electrophile E⁺.

Provide the major organic product of the following reaction sequence.

Provide the major organic product of the following reaction.

Provide the major organic product of the following reaction.

Name the major organic product which results when 3-ethylbenzenesulfonic acid is heated in aqueous acid.

In electrophilic aromatic substitution reactions the hydroxyl group is an o,p-director because ________.

When 2,4-dinitrochlorobenzene is treated with sodium hydroxide at 100°C followed by protonation ________.

Which of the following species is attacked by benzene in the electrophilic nitration reaction?

Exam 17: Reactions of Aromatic Compounds

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

Which of the following compounds undergoes reaction with HNO3/H2SO4 at the fastest rate?

Which of the following compounds will undergo bromination most rapidly using Br2, FeBr3?

What type of reaction is shown below? (Org. Lett., 2013, 15 (15) , 3950-3953)

Draw the major organic structure that results from the following sequence of reactions.

Provide the major organic product that results when benzene is treated with the following sequence of reagents: 1. HNO3, H2SO4 2. Br2, FeBr3.

Provide the major organic product(s) of the reaction shown below.

Draw the three major resonance structures of the sigma complex intermediate in the reaction of acetophenone with HNO3/H2SO4 to yield o-nitroacetophenone. Circle the resonance form which is less stable than the other two.

Provide a series of synthetic steps by which 3-bromoethylbenzene can be prepared from benzene.

Provide a series of synthetic steps by which 2-bromo-4-nitrobenzoic acid can be prepared from toluene.

Which of the following compounds would most likely be used in the preparation of isobutylbenzene from benzene?

Provide the structure of the major monoitration product of the compound below.

Provide the major resonance structures of the intermediate sigma complex in the reaction of benzene with the generic electrophile E+.

Provide the major organic product of the following reaction sequence.

Provide the major organic product of the following reaction.

Provide the major organic product of the following reaction.

Name the major organic product which results when 3-ethylbenzenesulfonic acid is heated in aqueous acid.

In electrophilic aromatic substitution reactions the hydroxyl group is an o,p-director because ________.

When 2,4-dinitrochlorobenzene is treated with sodium hydroxide at 100°C followed by protonation ________.

Which of the following species is attacked by benzene in the electrophilic nitration reaction?

Which of the following compounds undergoes reaction with HNO₃/H₂SO₄ at the fastest rate?

Which of the following compounds will undergo bromination most rapidly using Br₂, FeBr₃?

Provide the major organic product that results when benzene is treated with the following sequence of reagents: 1. HNO₃, H₂SO₄ 2. Br₂, FeBr₃.

Draw the three major resonance structures of the sigma complex intermediate in the reaction of acetophenone with HNO₃/H₂SO₄ to yield o-nitroacetophenone. Circle the resonance form which is less stable than the other two.

Provide the major resonance structures of the intermediate sigma complex in the reaction of benzene with the generic electrophile E⁺.