Question 1

Why does anisole undergo bromination with Br2 in the absence of FeBr3 whereas bromination of benzene requires the presence of FeBr3?

Accepted Answer

A)  anisole is a better nucleophile than benzene 
B)  the methoxy group of anisole is an inductive electron withdrawing substituent 
C)  Br2 is a good nucleophile 
D)  the reaction is accelerated by light 
A)  anisole is a better nucleophile than benzene 
B)  the methoxy group of anisole is an inductive electron withdrawing substituent 
C)  Br2 is a good nucleophile 
D)  the reaction is accelerated by light

Question 2

Which mechanism accounts for the reaction of chlorobenzene with acetyl chloride and AlCl3 to form 4-chloroacetophenone?

Accepted Answer

A)  Bimolecular nucleophilic substitution (SN2) 
B)  Nucleophilic aromatic substitution by elimination-addition 
C)  Nucleophilic aromatic substitution by addition-elimination 
D)  Electrophilic aromatic substitution 
A)  Bimolecular nucleophilic substitution (SN2) 
B)  Nucleophilic aromatic substitution by elimination-addition 
C)  Nucleophilic aromatic substitution by addition-elimination 
D)  Electrophilic aromatic substitution

Question 3

Which of the following undergoes the most rapid acylation upon treatment with acetyl chloride and AlCl3?

Accepted Answer

A)  benzene 
B)  toluene 
C)  chlorobenzene 
D)  1,4-dichlorobenzene 
A)  benzene 
B)  toluene 
C)  chlorobenzene 
D)  1,4-dichlorobenzene

Question 4

What is the major organic product obtained from the following reaction (assume that mixtures of ortho and para disubstituted compounds can be separated; continue the synthesis with either one)?

Accepted Answer

The answer of What is the major organic product obtained...

Question 5

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 6

Provide the structure (a single resonance contributor) of the key intermediate in the following reaction
.

Accepted Answer

The answer of Provide the structure (a single resonance contributor)...

Question 7

Which of the following is the reactive intermediate formed in the electrophilic bromination of toluene with Br2, FeBr3?

Accepted Answer

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

Question 8

What is the major organic product obtained from the following reaction?

Accepted Answer

The answer of What is the major organic product obtained...

Question 9

Which mechanism accounts for the reaction of benzyl chloride with sodium cyanide to form cyanomethylbenzene (phenylacetonitrile, PhCH2CN)?

Accepted Answer

A)  Bimolecular nucleophilic substitution (SN2) 
B)  Nucleophilic aromatic substitution by elimination-addition 
C)  Nucleophilic aromatic substitution by addition-elimination 
D)  Electrophilic aromatic substitution 
A)  Bimolecular nucleophilic substitution (SN2) 
B)  Nucleophilic aromatic substitution by elimination-addition 
C)  Nucleophilic aromatic substitution by addition-elimination 
D)  Electrophilic aromatic substitution

Question 10

Why does nitrobenzene fail to undergo Fieldel-Crafts alkylation with tert-butyl chloride and AlCl3?

Accepted Answer

A)  nitrobenzene reacts with AlCl3 
B)  nitrobenzene is a poor nucleophile 
C)  the nitro group is a strong electron donating group 
D)  the tert-butyl cation is a poor electrophile 
A)  nitrobenzene reacts with AlCl3 
B)  nitrobenzene is a poor nucleophile 
C)  the nitro group is a strong electron donating group 
D)  the tert-butyl cation is a poor electrophile

Question 11

Which of the following undergoes the most rapid nitration upon treatment with HNO3/H2SO4?

Accepted Answer

A)  toluene 
B)  benzene 
C)  bromobenzene 
D)  nitrobenzene 
A)  toluene 
B)  benzene 
C)  bromobenzene 
D)  nitrobenzene

Question 12

Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reactions?

Accepted Answer

A)  Cl, OH, CH2CH3 
B)  CH3, Br, COCH3 
C)  CH3, NH2, OH 
D)  COCH3, NO2, Br 
A)  Cl, OH, CH2CH3 
B)  CH3, Br, COCH3 
C)  CH3, NH2, OH 
D)  COCH3, NO2, Br

Question 13

What type of intermediate is formed in upon irradiation of a mixture of toluene and chlorine to give benzyl chloride?

Accepted Answer

A)  Meisenheimer complex 
B)  benzyne 
C)  cyclohexadienyl cation 
D)  benzyl radical 
A)  Meisenheimer complex 
B)  benzyne 
C)  cyclohexadienyl cation 
D)  benzyl radical

Question 14

Which of the following cannot be prepared from benzene in two synthetic steps?

Accepted Answer

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

Question 15

What is the major organic product obtained from the following sequence of reactions (if a reaction is likely to give you a mixture of ortho and para disubstituted compounds you should assume that they can be separated; continue the synthesis with either one)?

Accepted Answer

The answer of What is the major organic product obtained...

Question 16

Which of the following is not true about benzynes?

Accepted Answer

A)  They are planar 
B)  They are formed upon dehydrohalogenation of aryl halides 
C)  They are aromatic 
D)  They are intermediates in nucleophilic aromatic substitution reaction which take place by an addition-elimination mechanism 
A)  They are planar 
B)  They are formed upon dehydrohalogenation of aryl halides 
C)  They are aromatic 
D)  They are intermediates in nucleophilic aromatic substitution reaction which take place by an addition-elimination mechanism

Question 17

Which of the following sets of substituents are all meta directing in electrophilic aromatic substitution reactions?

Accepted Answer

A)  CH3, OH, Br 
B)  Cl, NH2, CN 
C)  COCH3, NO2, COOH 
D)  NH2, COCH3, OH 
A)  CH3, OH, Br 
B)  Cl, NH2, CN 
C)  COCH3, NO2, COOH 
D)  NH2, COCH3, OH

Question 18

Which of the following is not true about Meissenheimer complexes?

Accepted Answer

A)  They are resonance-stabilized anions 
B)  They are formed upon addition of a nucleophile to aryl halides 
C)  They are aromatic 
D)  They are intermediates in nucleophilic aromatic substitution reaction which take place by an addition-elimination mechanism 
A)  They are resonance-stabilized anions 
B)  They are formed upon addition of a nucleophile to aryl halides 
C)  They are aromatic 
D)  They are intermediates in nucleophilic aromatic substitution reaction which take place by an addition-elimination mechanism

Question 19

Which of the following chlorobenzenes produces a single isomer upon treatment with NaNH2?

Accepted Answer

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

Question 20

What is the major organic product obtained from the following sequence of reactions?

Accepted Answer

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

Exam 22: Reactions of Benzene and Its Derivatives

Why does anisole undergo bromination with Br2 in the absence of FeBr3 whereas bromination of benzene requires the presence of FeBr3?

Which mechanism accounts for the reaction of chlorobenzene with acetyl chloride and AlCl3 to form 4-chloroacetophenone?

Which of the following undergoes the most rapid acylation upon treatment with acetyl chloride and AlCl3?

What is the major organic product obtained from the following reaction (assume that mixtures of ortho and para disubstituted compounds can be separated; continue the synthesis with either one)?

What is the major organic product obtained from the following reaction?

Provide the structure (a single resonance contributor) of the key intermediate in the following reaction .

Which of the following is the reactive intermediate formed in the electrophilic bromination of toluene with Br2, FeBr3?

What is the major organic product obtained from the following reaction?

Which mechanism accounts for the reaction of benzyl chloride with sodium cyanide to form cyanomethylbenzene (phenylacetonitrile, PhCH2CN)?

Why does nitrobenzene fail to undergo Fieldel-Crafts alkylation with tert-butyl chloride and AlCl3?

Which of the following undergoes the most rapid nitration upon treatment with HNO3/H2SO4?

Which of the following sets of substituents are all deactivating groups in electrophilic aromatic substitution reactions?

What type of intermediate is formed in upon irradiation of a mixture of toluene and chlorine to give benzyl chloride?

Which of the following cannot be prepared from benzene in two synthetic steps?

What is the major organic product obtained from the following sequence of reactions (if a reaction is likely to give you a mixture of ortho and para disubstituted compounds you should assume that they can be separated; continue the synthesis with either one)?

Which of the following is not true about benzynes?

Which of the following sets of substituents are all meta directing in electrophilic aromatic substitution reactions?

Which of the following is not true about Meissenheimer complexes?

Which of the following chlorobenzenes produces a single isomer upon treatment with NaNH2?

What is the major organic product obtained from the following sequence of reactions?

Covalent Bonding and Shapes of Molecules

Alkanes and Cycloalkanes

Stereoisomerism and Chirality

Acids and Bases

Alkenes: Bonding, Nomenclature, and Properties

Reactions of Alkenes

Alkynes

Haloalkanes, Halogenation, and Radical Reactions

Nucleophilic Substitution and Beta-Elimination

Alcohols

Ethers, Epoxides, and Sulfides

Infrared Spectroscopy

Nuclear Magnetic Resonance Spectroscopy

Mass Spectrometry

An Introduction to Organometallic Compounds

Aldehydes and Ketones

Carboxylic Acids

Functional Derivatives of Carboxylic Acids

Enolate Anions and Enamines

Dienes, Conjugated Systems, and Pericyclic Reactions

Benzene and the Concept of Aromaticity

Filters

Why does anisole undergo bromination with Br₂ in the absence of FeBr₃ whereas bromination of benzene requires the presence of FeBr₃?

Which mechanism accounts for the reaction of chlorobenzene with acetyl chloride and AlCl₃ to form 4-chloroacetophenone?

Which of the following undergoes the most rapid acylation upon treatment with acetyl chloride and AlCl₃?

Which of the following is the reactive intermediate formed in the electrophilic bromination of toluene with Br₂, FeBr₃?

Which mechanism accounts for the reaction of benzyl chloride with sodium cyanide to form cyanomethylbenzene (phenylacetonitrile, PhCH₂CN)?

Why does nitrobenzene fail to undergo Fieldel-Crafts alkylation with tert-butyl chloride and AlCl₃?

Which of the following undergoes the most rapid nitration upon treatment with HNO₃/H₂SO₄?

Which of the following chlorobenzenes produces a single isomer upon treatment with NaNH₂?