Question 1

What would be the product of the following reaction sequence?

Accepted Answer

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

Question 2

What would be the product of the following reaction sequence?

Accepted Answer

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

Question 3

Which of the following compounds would be most reactive to ring bromination?

Accepted Answer

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

Question 4

Which would be the major product(s)of the following reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) I and II in roughly equal amounts. 
E) I and III in roughly equal amounts. 
A) I 
B) II 
C) III 
D) I and II in roughly equal amounts. 
E) I and III in roughly equal amounts.

Question 5

What would be the major product of the following reaction?

Accepted Answer

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

Question 6

Which of the following compounds would you expect to be most reactive toward ring nitration?

Accepted Answer

A) Benzene 
B) Toluene 
C) m-Xylene 
D) o-Xylene 
E) Benzoic acid 
A) Benzene 
B) Toluene 
C) m-Xylene 
D) o-Xylene 
E) Benzoic acid

Question 7

What would be the product of the following reaction sequence?

Accepted Answer

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

Question 8

Which is the best sequence of reactions for the following transformation?

Accepted Answer

A) i)HNO3,H2SO4; ii)2EtMgBr,Et2O; iii)NH4Cl 
B) i)2EtMgBr,Et2O; ii)H3O+; iii)HNO3,H2SO4 
C) i)HNO3,H2SO4; ii)NaBH4,H2O; iii)2EtMgBr,Et2O 
D) i)LAH; ii)2EtLi,Et2O; iii)HNO3,H2SO4,heat 
E) None of these syntheses is satisfactory. 
A) i)HNO3,H2SO4; ii)2EtMgBr,Et2O; iii)NH4Cl 
B) i)2EtMgBr,Et2O; ii)H3O+; iii)HNO3,H2SO4 
C) i)HNO3,H2SO4; ii)NaBH4,H2O; iii)2EtMgBr,Et2O 
D) i)LAH; ii)2EtLi,Et2O; iii)HNO3,H2SO4,heat 
E) None of these syntheses is satisfactory.

Question 9

What would be the major product(s)of the following reaction?

Accepted Answer

A) I 
B) II 
C) III 
D) Equal amounts of I and IV. 
E) Equal amounts of II and IV. 
A) I 
B) II 
C) III 
D) Equal amounts of I and IV. 
E) Equal amounts of II and IV.

Question 10

The reaction of benzene with   in the presence of anhydrous aluminum chloride produces principally which of these?

Accepted Answer

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

Question 11

Which of the following reactions could be used to synthesize tert-butylbenzene?

Accepted Answer

A)    
B)    
C)    
D) All of these choices. 
E) None of these choices. 
A)    
B)    
C)    
D) All of these choices. 
E) None of these choices.

Question 12

The major product(s),A,of the following reaction,   would be:

Accepted Answer

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

Question 13

What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and AlCl3?

Accepted Answer

A) butylbenzene 
B) 2-phenylbutane 
C) 2-methyl-1-phenylpropane 
D) t-butylbenzene 
E) 2,2-diphenylbutane 
A) butylbenzene 
B) 2-phenylbutane 
C) 2-methyl-1-phenylpropane 
D) t-butylbenzene 
E) 2,2-diphenylbutane

Question 14

Which of the following compounds would be most reactive toward electrophilic substitution?

Accepted Answer

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

Question 15

Which of the following is not an ortho-para director in electrophilic aromatic substitution?

Accepted Answer

A)    
B) -OCH3 
C) -CH3 
D) -F 
E) -NH2 
A)    
B) -OCH3 
C) -CH3 
D) -F 
E) -NH2

Question 16

Which of these is a satisfactory synthesis of 1-chloro-2-phenylethane?

Accepted Answer

A) C6H5CH2CH3 + Cl2,Fe $\to$ 
B) C6H5CH2CH3 + Cl2,400S1U1P1$\circ$S1S1P0C $\to$ 
C) C6H5CH2CH2OH + SOCl2 $\to$ 
D) C6H5CH=CH2 + HCl,peroxide $\to$ 
E) C6H6 + CH3CH2Cl,AlCl3 $\to$ 
A) C6H5CH2CH3 + Cl2,Fe $\to$ 
B) C6H5CH2CH3 + Cl2,400S1U1P1$\circ$S1S1P0C $\to$ 
C) C6H5CH2CH2OH + SOCl2 $\to$ 
D) C6H5CH=CH2 + HCl,peroxide $\to$ 
E) C6H6 + CH3CH2Cl,AlCl3 $\to$

Question 17

Consider the following reaction: what is the expected product?

Accepted Answer

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

Question 18

This substituent deactivates the benzene ring towards electrophilic substitution but directs the incoming group chiefly to the ortho and para positions.

Accepted Answer

A) -OCH2CH3 
B) -NO2 
C) -F 
D) -CF3 
E) -NHCOCH3 
A) -OCH2CH3 
B) -NO2 
C) -F 
D) -CF3 
E) -NHCOCH3

Question 19

What would you expect to be the major product obtained from the following reaction?

Accepted Answer

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

Question 20

Which of the following is not an ortho-para director in electrophilic aromatic substitution?

Accepted Answer

A) -CF3 
B) -OCH3 
C) -CH3 
D) -F 
E) -NH2 
A) -CF3 
B) -OCH3 
C) -CH3 
D) -F 
E) -NH2

Exam 15: Reactions of Aromatic Compounds

What would be the product of the following reaction sequence?

What would be the product of the following reaction sequence?

Which of the following compounds would be most reactive to ring bromination?

Which would be the major product(s)of the following reaction?

What would be the major product of the following reaction?

Which of the following compounds would you expect to be most reactive toward ring nitration?

What would be the product of the following reaction sequence?

Which is the best sequence of reactions for the following transformation?

What would be the major product(s)of the following reaction?

The reaction of benzene with in the presence of anhydrous aluminum chloride produces principally which of these?

Which of the following reactions could be used to synthesize tert-butylbenzene?

The major product(s),A,of the following reaction, would be:

What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and AlCl3?

Which of the following compounds would be most reactive toward electrophilic substitution?

Which of the following is not an ortho-para director in electrophilic aromatic substitution?

Which of these is a satisfactory synthesis of 1-chloro-2-phenylethane?

Consider the following reaction: what is the expected product?

This substituent deactivates the benzene ring towards electrophilic substitution but directs the incoming group chiefly to the ortho and para positions.

What would you expect to be the major product obtained from the following reaction?

Which of the following is not an ortho-para director in electrophilic aromatic substitution?

The Basics

Families of Carbon

Acids and Bases

Nomenclature and Conformations of Alkanes and Cycloalkanes

Stereochemistry

Nucleophilic Reactions

Alkenes and Alkynes I

Alkenes and Alkynes II

Nuclear Magnetic Resonance and Mass Spectrometry

Radical Reactions

Alcohols and Ethers

Alcohols From Carbonyl Compounds

Conjugated Unsaturated Systems

Aromatic Compounds

Aldehydes and Ketones

Carboxylic Acids and Their Derivatives

Reactions at the Α Carbon of Carbonyl Compounds

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

Amines

Transition Metal Complexes

Carbohydrates

Lipids

Amino Acids and Proteins

Nucleic Acids and Protein Synthesis

Filters

What is the chief product of the Friedel-Crafts alkylation of benzene with 1-butene and AlCl₃?