Question 1

What is the product of the following monobromonation reaction?

Accepted Answer

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

Question 2

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 3

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 4

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 5

What are the two distinct pathways for nucleophilic aromatic substitution?

Accepted Answer

A) Addition-substitution and substitution-addition 
B) Addition-elimination and elimination-addition 
C) Addition-addition and elimination-elimination 
D) Elimination-substitution and substitution-elimination 
A) Addition-substitution and substitution-addition 
B) Addition-elimination and elimination-addition 
C) Addition-addition and elimination-elimination 
D) Elimination-substitution and substitution-elimination

Question 6

Which set of reagents would most likely bring about the following transformation?

Accepted Answer

A) Br2 and FeBr3 
B) NBS and light 
C) Br2 in CCl4 
D) NaBr and H2O 
A) Br2 and FeBr3 
B) NBS and light 
C) Br2 in CCl4 
D) NaBr and H2O

Question 7

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 8

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 9

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 10

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 11

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 12

What is the best choice of reagent to bring about the following transformation?

Accepted Answer

A) [1] LiAlH4; [2] H2O 
B) Zn (Hg),HCl 
C) NH3,NaOH 
D) H2,Pd-C 
A) [1] LiAlH4; [2] H2O 
B) Zn (Hg),HCl 
C) NH3,NaOH 
D) H2,Pd-C

Question 13

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 14

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 15

Which of the following substituents are activators in electrophilic aromatic substitution?

Accepted Answer

A) CH3O ¾ 
B) Cl ¾ 
C) NO2 ¾ 
D) HSO3¾ 
A) CH3O ¾ 
B) Cl ¾ 
C) NO2 ¾ 
D) HSO3¾

Question 16

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 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

Which of the following halides will not work as an electrophile in a Friedel-Crafts alkylation reaction?

Accepted Answer

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

Question 19

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 20

What is the structure of compound A?

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 product of the following monobromonation reaction?

What is the major organic product of the following reaction?

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

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

What are the two distinct pathways for nucleophilic aromatic substitution?

Which set of reagents would most likely bring about the following transformation?

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

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

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

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

What is the major organic product of the following reaction?

What is the best choice of reagent to bring about the following transformation?

What is the product of the following reaction?

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

Which of the following substituents are activators in electrophilic aromatic substitution?

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

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

Which of the following halides will not work as an electrophile in a Friedel-Crafts alkylation reaction?

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

What is the structure of compound A?

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

Spectroscopy A: Mass Spectrometry

Spectroscopy B: Infrared Spectroscopy

Spectroscopy C: Nuclear Magnetic Resonance Spectroscopy

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