Question 1

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 2

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 3

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 4

Provide the structure (a single resonance contributor) of the key intermediate in the electrophilic aromatic nitration of chlorobenzene.

Accepted Answer

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

Question 5

Which of the following reactions or reaction sequences will not give isopropylbenzene as the major product?

Accepted Answer

A)  treatment of benzene with isopropyl alcohol and HF 
B)  treatment of benzene with 1-chloropropane and AlCl3 
C)  treatment of benzene with propanoyl chloride and AlCl3; followed by reaction with Zn(Hg) and HCl 
D)  treatment of benzene with 1-propene and HF 
A)  treatment of benzene with isopropyl alcohol and HF 
B)  treatment of benzene with 1-chloropropane and AlCl3 
C)  treatment of benzene with propanoyl chloride and AlCl3; followed by reaction with Zn(Hg) and HCl 
D)  treatment of benzene with 1-propene and HF

Question 6

What is the electrophile in the reaction of benzene with acetyl chloride, CH3COCl, and AlCl3?

Accepted Answer

A)  CH3C≡O+ 
B)  CH3+ 
C)  CH3CO2− 
D)  benzene 
A)  CH3C≡O+ 
B)  CH3+ 
C)  CH3CO2− 
D)  benzene

Question 7

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 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 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 10

The predominant intermediate in the electrophilic nitration of benzenesulfonic acid is shown below.

Accepted Answer

A) True 
 B)False

Question 11

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 12

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 13

Which of the following is the reactive intermediate in the nucleophilic substitution of 4-bromo-1-nitrobenzene with sodium hydroxide?

Accepted Answer

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

Question 14

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

Accepted Answer

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

Question 15

Which of the following reactions or sequences will provide 1-propylbenzene as the major product?

Accepted Answer

A)  treatment of benzene with isopropyl alcohol and HF 
B)  treatment of benzene with propanoyl chloride and AlCl3; followed by reaction with Zn(Hg) and HCl 
C)  treatment of benzene with 1-chloropropane and AlCl3 
D)  treatment of benzene with 1-propene and HF 
A)  treatment of benzene with isopropyl alcohol and HF 
B)  treatment of benzene with propanoyl chloride and AlCl3; followed by reaction with Zn(Hg) and HCl 
C)  treatment of benzene with 1-chloropropane and AlCl3 
D)  treatment of benzene with 1-propene and HF

Question 16

The electrophile that could be used to make acetophenone (methyl phenyl ketone) from benzene is shown below. $\mathrm{CH}_{3} \stackrel{+}{\mathrm{C}} \mathrm{O}$

Accepted Answer

A) True 
 B)False

Question 17

What is "X" in the following reaction? ​

Accepted Answer

A)  H2Cr2O4 
B)  H2 
C)  LiAlH4 
D)  H2/Pt 
A)  H2Cr2O4 
B)  H2 
C)  LiAlH4 
D)  H2/Pt

Question 18

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 19

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

Accepted Answer

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

Question 20

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

Exam 22: Reactions of Benzene and Its Derivatives

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

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

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

Provide the structure (a single resonance contributor) of the key intermediate in the electrophilic aromatic nitration of chlorobenzene.

Which of the following reactions or reaction sequences will not give isopropylbenzene as the major product?

What is the electrophile in the reaction of benzene with acetyl chloride, CH3COCl, and AlCl3?

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

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

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

The predominant intermediate in the electrophilic nitration of benzenesulfonic acid is shown below.

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

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 the reactive intermediate in the nucleophilic substitution of 4-bromo-1-nitrobenzene with sodium hydroxide?

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

Which of the following reactions or sequences will provide 1-propylbenzene as the major product?

The electrophile that could be used to make acetophenone (methyl phenyl ketone) from benzene is shown below. CH3C+O\mathrm{CH}_{3} \stackrel{+}{\mathrm{C}} \mathrm{O}CH3​C+​O

What is "X" in the following reaction? ​

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

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

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

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

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

What is the electrophile in the reaction of benzene with acetyl chloride, CH₃COCl, and AlCl₃?

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

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

The electrophile that could be used to make acetophenone (methyl phenyl ketone) from benzene is shown below. $\mathrm{CH}_{3} \stackrel{+}{\mathrm{C}} \mathrm{O}$

What is "X" in the following reaction?