Question 1

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

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 2

What is the electrophile in the Friedel-Crafts alkylation reaction with tert-butylchloride?

Accepted Answer

A) The tert-butyl cation 
B) A complex of tert-butylchloride and aluminum chloride 
C) A proton 
D) Aluminum chloride 
A) The tert-butyl cation 
B) A complex of tert-butylchloride and aluminum chloride 
C) A proton 
D) Aluminum chloride

Question 3

What is (are)the product(s)of the following reaction?

Accepted Answer

A) Only I 
B) Only II 
C) Only III 
D) Only I and II 
A) Only I 
B) Only II 
C) Only III 
D) Only I and II

Question 4

What is the reactive intermediate formed in the addition-elimination mechanism of nucleophilic aromatic substitution?

Accepted Answer

A) Carbocation 
B) Radical 
C) Benzyne 
D) Carbanion 
A) Carbocation 
B) Radical 
C) Benzyne 
D) Carbanion

Question 5

Which of the following statements about the mechanism of electrophilic aromatic substitution is not true?

Accepted Answer

A) All electrophilic aromatic substitution reactions occur via a two-step mechanism. 
B) The transition state of the first step is lower in energy. 
C) The first step is the rate-determining step. 
D) The second step is the fast step. 
A) All electrophilic aromatic substitution reactions occur via a two-step mechanism. 
B) The transition state of the first step is lower in energy. 
C) The first step is the rate-determining step. 
D) The second step is the fast step.

Question 6

What will be the site that leads to the major mono substitution product for an electrophilic aromatic substitution reaction of the following compound?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 7

What is the electrophile in aromatic sulfonation?

Accepted Answer

A) H2SO3 
B) H2SO4 
C) SO3+ 
D) HSO3+ 
A) H2SO3 
B) H2SO4 
C) SO3+ 
D) HSO3+

Question 8

What is the product of the following reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 9

What is the major organic product of the following reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 10

Which of the following statements about nucleophilic aromatic substitution is not true?

Accepted Answer

A) Increasing the electronegativity of the halogen increases the reactivity of the aryl halide. 
B) Increasing the number of electron-withdrawing groups increases the reactivity of the aryl halide. 
C) Electron-withdrawing groups stabilize the intermediate carbanion,and lower the energy of the transition state. 
D) When a nitro group is located meta to the halogen,the negative charge of the intermediate carbanion can be delocalized onto the NO2 group,thus stabilizing it. 
A) Increasing the electronegativity of the halogen increases the reactivity of the aryl halide. 
B) Increasing the number of electron-withdrawing groups increases the reactivity of the aryl halide. 
C) Electron-withdrawing groups stabilize the intermediate carbanion,and lower the energy of the transition state. 
D) When a nitro group is located meta to the halogen,the negative charge of the intermediate carbanion can be delocalized onto the NO2 group,thus stabilizing it.

Question 11

What is a major problem with Friedel-Crafts alkylation?

Accepted Answer

A) It requires high temperatures. 
B) The conditions are too acidic. 
C) The starting material is frequently over-alkylated. 
D) The products coordinate with the aluminum chloride. 
A) It requires high temperatures. 
B) The conditions are too acidic. 
C) The starting material is frequently over-alkylated. 
D) The products coordinate with the aluminum chloride.

Question 12

What is the first step in the general mechanism for electrophilic aromatic substitution?

Accepted Answer

A) Protonation of the aromatic ring 
B) Deprotonation of the aromatic ring 
C) Addition of the electrophile to the aromatic ring 
D) Loss of the electrophile from the aromatic ring 
A) Protonation of the aromatic ring 
B) Deprotonation of the aromatic ring 
C) Addition of the electrophile to the aromatic ring 
D) Loss of the electrophile from the aromatic ring

Question 13

Consider the tetracyclic aromatic compound drawn below,with rings labelled as I,II,III,and IV.Which of the four rings is most reactive in electrophilic aromatic substitution?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 14

Rank the following compounds in order of increasing reactivity in nucleophilic aromatic substitution.

Accepted Answer

A) III < II < I 
B) I < II < III 
C) III < I < II 
D) I < III < II 
A) III < II < I 
B) I < II < III 
C) III < I < II 
D) I < III < II

Question 15

Rank the following compounds in order of increasing reactivity in electrophilic aromatic substitution.

Accepted Answer

A) I < II < III < IV 
B) II < I < IV < III 
C) III < IV < I < II 
D) II < I < III < IV 
A) I < II < III < IV 
B) II < I < IV < III 
C) III < IV < I < II 
D) II < I < III < IV

Question 16

Rank the following deactivating groups in order of increasing deactivating strength,listing the least deactivating first.

Accepted Answer

A) I < II < III < IV 
B) II < III < IV < I 
C) II < I < III < IV 
D) IV < III < I < II 
A) I < II < III < IV 
B) II < III < IV < I 
C) II < I < III < IV 
D) IV < III < I < II

Question 17

Which of the following substituents is an ortho,para director?

Accepted Answer

A) ¾ CHO 
B) ¾ COOH 
C) ¾ NHCOR 
D) ¾ CN 
A) ¾ CHO 
B) ¾ COOH 
C) ¾ NHCOR 
D) ¾ CN

Question 18

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

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 19

What is the major product of the following reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Question 20

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

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
A) I 
B) II 
C) III 
D) IV

Exam 16: Reactions of Aromatic Compounds

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

What is the electrophile in the Friedel-Crafts alkylation reaction with tert-butylchloride?

What is (are)the product(s)of the following reaction?

What is the reactive intermediate formed in the addition-elimination mechanism of nucleophilic aromatic substitution?

Which of the following statements about the mechanism of electrophilic aromatic substitution is not true?

What will be the site that leads to the major mono substitution product for an electrophilic aromatic substitution reaction of the following compound?

What is the electrophile in aromatic sulfonation?

What is the product of the following reaction?

What is the major organic product of the following reaction?

Which of the following statements about nucleophilic aromatic substitution is not true?

What is a major problem with Friedel-Crafts alkylation?

What is the first step in the general mechanism for electrophilic aromatic substitution?

Consider the tetracyclic aromatic compound drawn below,with rings labelled as I,II,III,and IV.Which of the four rings is most reactive in electrophilic aromatic substitution?

Rank the following compounds in order of increasing reactivity in nucleophilic aromatic substitution.

Rank the following compounds in order of increasing reactivity in electrophilic aromatic substitution.

Rank the following deactivating groups in order of increasing deactivating strength,listing the least deactivating first.

Which of the following substituents is an ortho,para director?

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

What is the major product of the following reaction?

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

Structure and Bonding

Acids and Bases

Introduction to Organic Molecules and Functional Groups

Alkanes

Stereochemistry

Understanding Organic Reactions

Alkyl Halides and Nucleophilic Substitution

Alkyl Halides and Elimination Reactions

Alcohols,ethers,and Related Compounds

Alkenes and Addition Reactions

Alkynes and Synthesis

Oxidation and Reduction

Radical Reactions

Conjugation, resonance, and Dienes

Benzene and Aromatic Compounds

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Aldehydes and Ketones - Nucleophilic Addition

Carboxylic Acids and the Acidity of the O-H Bond

Carboxylic Acids and Their Derivatives - Nucleophilic Acyl Substitution

Substitution Reactions of Carbonyl Compounds at the a Carbon

Carbonyl Condensation Reactions

Amines

Carbon-Carbon Bond-Forming Reactions in Organic Synthesis

Pericyclic Reactions

Carbohydrates

Amino Acids and Proteins

Synthetic Polymers

Lipids

Molecular Ion Peaks and Fragmentation Patterns

Analyzing Molecular Motion and Infrared Spectroscopy

Organic Spectroscopy Concepts

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