Question 1

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 2

The compound 4-bromo-1-propylbenzene is best made from benzene by the application of these reagents in the order shown:

Accepted Answer

A) (1)Br2,Fe (2)CH3CH2CH2Cl,AlCl3 
B) (1)CH3CH2CH2Cl,AlCl3 (2)Br2,Fe 
C)    
D)    
E) (1)(CH3)2CHCl,AlCl3 (2)Br2,Fe 
A) (1)Br2,Fe (2)CH3CH2CH2Cl,AlCl3 
B) (1)CH3CH2CH2Cl,AlCl3 (2)Br2,Fe 
C)    
D)    
E) (1)(CH3)2CHCl,AlCl3 (2)Br2,Fe

Question 3

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

Accepted Answer

A) i)SOCl2; ii)C6H6,AlCl3; iii)Zn(Hg),HCl; iv)HNO3,H2SO4 
B) i)SOCl2; ii)HNO3,H2SO4; iii)C6H6,AlCl3; iv)H2,Ni 
C) i)HNO3,H2SO4; ii)SOCl2; iii)C6H6,AlCl3; iv)Zn(Hg),HCl 
D) i)PBr3; ii)HNO3,H2SO4; iii)C6H6,AlCl3; iv)NaBH4,H2O 
E) Two of these syntheses are satisfactory. 
A) i)SOCl2; ii)C6H6,AlCl3; iii)Zn(Hg),HCl; iv)HNO3,H2SO4 
B) i)SOCl2; ii)HNO3,H2SO4; iii)C6H6,AlCl3; iv)H2,Ni 
C) i)HNO3,H2SO4; ii)SOCl2; iii)C6H6,AlCl3; iv)Zn(Hg),HCl 
D) i)PBr3; ii)HNO3,H2SO4; iii)C6H6,AlCl3; iv)NaBH4,H2O 
E) Two of these syntheses are satisfactory.

Question 4

Which of the following contributors to the resonance stabilized hybrid formed when aniline undergoes para-chlorination would be exceptionally stable?

Accepted Answer

A) I 
B) II 
C) III 
D) IV 
E) None of these choices. 
A) I 
B) II 
C) III 
D) IV 
E) None of these choices.

Question 5

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 6

Based on your knowledge of electrophilic aromatic substitution,predict the preferential position of attack of an electrophile on furan,i.e.,does the electrophile E+ attack carbon 2,or 3? Explain your answer.   Which substitution product forms preferentially and why?

Accepted Answer

The 2 substitution product is favored si

Question 7

Arrange the following compounds in order of decreasing reactivity in electrophilic substitution:

Accepted Answer

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

Question 8

Benzoic acid can be prepared by the oxidation of which of the following compounds:

Accepted Answer

A) C6H5CH=CH2 
B) C6H5C$\equiv$CH 
C) C6H5COCH3 
D) C6H5CH2CH2CH3 
E) All of these choices. 
A) C6H5CH=CH2 
B) C6H5C$\equiv$CH 
C) C6H5COCH3 
D) C6H5CH2CH2CH3 
E) All of these choices.

Question 9

What would you expect to be the major product(s)obtained from the mononitration of m-dichlorobenzene?

Accepted Answer

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

Question 10

Which reagent(s)would you use to synthesize 2- and 4-bromo-1-cyclopentylbenzene from cyclopentylbenzene?

Accepted Answer

A) N-Bromosuccinimide (NBS),CCl4,light 
B) PBr3 
C) Br2,FeBr3 
D) CH3CH2Br,AlBr3 
E) HBr,ROOR 
A) N-Bromosuccinimide (NBS),CCl4,light 
B) PBr3 
C) Br2,FeBr3 
D) CH3CH2Br,AlBr3 
E) HBr,ROOR

Question 11

(Trifluoromethyl)benzene,C6H5CF3,will

Accepted Answer

A) nitrate rapidly in the ortho-para positions. 
B) nitrate slowly in the ortho-para positions. 
C) nitrate rapidly in the meta position. 
D) nitrate slowly in the meta position. 
E) fail to nitrate under any conditions. 
A) nitrate rapidly in the ortho-para positions. 
B) nitrate slowly in the ortho-para positions. 
C) nitrate rapidly in the meta position. 
D) nitrate slowly in the meta position. 
E) fail to nitrate under any conditions.

Question 12

What is the Birch reduction 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 13

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 14

When the following substance is treated with Br2/FeBr3,the major product is obtained in good yield,and only very small amounts of minor products are found.What is this major product and why are the minor products not formed to any significant degree? Explain clearly.

Accepted Answer

The major products are produced by bromi

Question 15

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 16

A mixture of chlorobenzene (1 mol)and anisole (1mol)is allowed to react with Br2 (0.5 mol)in the presence of trace amounts of FeBr3.What is the principal product of the competing reactions?

Accepted Answer

A) 1-bromo-4-chlorobenzene 
B) 1-bromo-2-chlorobenzene 
C) 1-bromo-3-chlorobenzene 
D) 4-bromoanisole 
E) 3-bromoanisole 
A) 1-bromo-4-chlorobenzene 
B) 1-bromo-2-chlorobenzene 
C) 1-bromo-3-chlorobenzene 
D) 4-bromoanisole 
E) 3-bromoanisole

Question 17

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

Accepted Answer

A) C6H5CH2CH3 + Br2,Fe3+ $\to$ 
B) C6H5CH2CH3 + Br2,400S1U1P1$\circ$S1S1P0C $\to$ 
C) C6H5CH2CH2OH + Br2,CCl4 $\to$ 
D) C6H5CH=CH2 + HBr,ROOR $\to$ 
E) C6H5CH2CH3 + NBS,ROOR $\to$ 
A) C6H5CH2CH3 + Br2,Fe3+ $\to$ 
B) C6H5CH2CH3 + Br2,400S1U1P1$\circ$S1S1P0C $\to$ 
C) C6H5CH2CH2OH + Br2,CCl4 $\to$ 
D) C6H5CH=CH2 + HBr,ROOR $\to$ 
E) C6H5CH2CH3 + NBS,ROOR $\to$

Question 18

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

Accepted Answer

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

Question 19

Which reagent(s)would you use to carry out the following transformation? ethylbenzene $\to$ 2- and 4-chloro-1-ethylbenzene

Accepted Answer

A) Cl2,light,and heat 
B) Cl2,FeCl3 
C) SOCl2 
D) C2H5Cl,AlCl3 
E) None of these choices. 
A) Cl2,light,and heat 
B) Cl2,FeCl3 
C) SOCl2 
D) C2H5Cl,AlCl3 
E) None of these choices.

Question 20

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

Exam 15: Reactions of Aromatic Compounds

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

The compound 4-bromo-1-propylbenzene is best made from benzene by the application of these reagents in the order shown:

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

Which of the following contributors to the resonance stabilized hybrid formed when aniline undergoes para-chlorination would be exceptionally stable?

What would be the product of the following reaction sequence?

Based on your knowledge of electrophilic aromatic substitution,predict the preferential position of attack of an electrophile on furan,i.e.,does the electrophile E+ attack carbon 2,or 3? Explain your answer. Which substitution product forms preferentially and why?

Arrange the following compounds in order of decreasing reactivity in electrophilic substitution:

Benzoic acid can be prepared by the oxidation of which of the following compounds:

What would you expect to be the major product(s)obtained from the mononitration of m-dichlorobenzene?

Which reagent(s)would you use to synthesize 2- and 4-bromo-1-cyclopentylbenzene from cyclopentylbenzene?

(Trifluoromethyl)benzene,C6H5CF3,will

What is the Birch reduction product of the following reaction?

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

When the following substance is treated with Br2/FeBr3,the major product is obtained in good yield,and only very small amounts of minor products are found.What is this major product and why are the minor products not formed to any significant degree? Explain clearly.

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

A mixture of chlorobenzene (1 mol)and anisole (1mol)is allowed to react with Br2 (0.5 mol)in the presence of trace amounts of FeBr3.What is the principal product of the competing reactions?

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

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

Which reagent(s)would you use to carry out the following transformation? ethylbenzene →\to→ 2- and 4-chloro-1-ethylbenzene

What would be the major product of the following reaction?

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

Based on your knowledge of electrophilic aromatic substitution,predict the preferential position of attack of an electrophile on furan,i.e.,does the electrophile E⁺ attack carbon 2,or 3? Explain your answer. Which substitution product forms preferentially and why?

(Trifluoromethyl)benzene,C₆H₅CF₃,will

When the following substance is treated with Br₂/FeBr₃,the major product is obtained in good yield,and only very small amounts of minor products are found.What is this major product and why are the minor products not formed to any significant degree? Explain clearly.

A mixture of chlorobenzene (1 mol)and anisole (1mol)is allowed to react with Br₂ (0.5 mol)in the presence of trace amounts of FeBr₃.What is the principal product of the competing reactions?

Which reagent(s)would you use to carry out the following transformation? ethylbenzene $\to$ 2- and 4-chloro-1-ethylbenzene