Question 1

An example of a metal-reducing agent is _____.

Accepted Answer

A)  zinc 
B)  xenon 
C)  radon 
D)  selenium 
A)  zinc 
B)  xenon 
C)  radon 
D)  selenium

Question 2

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

Accepted Answer

A)  CH3, OCH3, COCH3 
B)  Cl, CN, NO2 
C)  Cl, NH2, CH3 
D)  CH3, NH2, OCH3 
A)  CH3, OCH3, COCH3 
B)  Cl, CN, NO2 
C)  Cl, NH2, CH3 
D)  CH3, NH2, OCH3

Question 3

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 4

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

Accepted Answer

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

Question 5

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 6

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

Accepted Answer

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

Question 7

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 8

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

Question 9

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 10

What is the major organic product obtained from the following reaction (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 11

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 12

Which of the following undergoes the most rapid bromination upon treatment with Br2/FeBr3?

Accepted Answer

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

Question 13

Identify "X" in the given reaction. ​

Accepted Answer

A)  3-methyl-2-propanol 
B)  2-methyl-2-butanol 
C)  2-methyl-2-propanol 
D)  3-methyl-2-butanol 
A)  3-methyl-2-propanol 
B)  2-methyl-2-butanol 
C)  2-methyl-2-propanol 
D)  3-methyl-2-butanol

Question 14

Which of the following compounds undergoes the most rapid nucleophilic substitution with hydroxide ion?

Accepted Answer

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

Question 15

What is the role of FeBr3 in electrophilic aromatic bromination of benzene using Br2?

Accepted Answer

A)  nucleophile 
B)  electrophile 
C)  Lewis acid 
D)  base 
A)  nucleophile 
B)  electrophile 
C)  Lewis acid 
D)  base

Question 16

All of the following can act as an electrophile in an electrophilic aromatic substitution reaction.
SO3 (CH3)3C+ NO2+

Accepted Answer

A) True 
 B)False

Question 17

The best sequence in which to carry out the following reaction is 1) Br2, AlBr3, 2) H2SO4, SO3.

Accepted Answer

A) True 
 B)False

Question 18

What type of intermediate is formed in the reaction between chlorobenzene and tert-butyl chloride and AlCl3 to give 4-chloro-1-tert-butylbenzene?

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 19

Which of the following sets of substituents are all ortho/para directing in electrophilic aromatic substitution reactions?

Accepted Answer

A)  Br, CH3, NO2 
B)  CH3, NH2, Br 
C)  Cl, OCH3, COCH3 
D)  NO2, COCH3, COOH 
A)  Br, CH3, NO2 
B)  CH3, NH2, Br 
C)  Cl, OCH3, COCH3 
D)  NO2, COCH3, COOH

Question 20

What type of intermediate is formed in the reaction between bromobenzene and sodium amide to give aniline?

Accepted Answer

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

Exam 22: Reactions of Benzene and Its Derivatives

An example of a metal-reducing agent is _____.

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

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

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

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

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.

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

Which of the following is not true about benzynes?

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

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)?

Which of the following undergoes the most rapid bromination upon treatment with Br2/FeBr3?

Identify "X" in the given reaction. ​

Which of the following compounds undergoes the most rapid nucleophilic substitution with hydroxide ion?

What is the role of FeBr3 in electrophilic aromatic bromination of benzene using Br2?

All of the following can act as an electrophile in an electrophilic aromatic substitution reaction. SO3 (CH3)3C+ NO2+

The best sequence in which to carry out the following reaction is 1) Br2, AlBr3, 2) H2SO4, SO3.

What type of intermediate is formed in the reaction between chlorobenzene and tert-butyl chloride and AlCl3 to give 4-chloro-1-tert-butylbenzene?

Which of the following sets of substituents are all ortho/para directing in electrophilic aromatic substitution reactions?

What type of intermediate is formed in the reaction between bromobenzene and sodium amide to give aniline?

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

Amines

Catalytic Carbon-Carbon Bond Formation

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids

Organic Polymer Chemistry

Filters

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

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

Which of the following undergoes the most rapid bromination upon treatment with Br₂/FeBr₃?

Identify "X" in the given reaction.

What is the role of FeBr₃ in electrophilic aromatic bromination of benzene using Br₂?

All of the following can act as an electrophile in an electrophilic aromatic substitution reaction. SO₃(CH₃)₃C⁺ NO₂⁺

The best sequence in which to carry out the following reaction is 1) Br₂, AlBr₃, 2) H₂SO₄, SO₃.

What type of intermediate is formed in the reaction between chlorobenzene and tert-butyl chloride and AlCl₃ to give 4-chloro-1-tert-butylbenzene?