Question 1

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. F) A) and D)
G) A) and C)

Question 2

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 3

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-bromoanisoleF) None of the above
G) D) and E)

Question 4

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)   2,Fe (2) CH3CH2CH2Cl,AlCl3 
B)  (1) CH3CH2CH2Cl,AlCl3 (2) Br2,Fe 
C)     
D)     
E)  (1) (CH3) 2CHCl,AlCl3 (2) Br2,Fe" class="answers-bank-image d-inline" rel="preload" >
D)   2,Fe (2) CH3CH2CH2Cl,AlCl3 
B)  (1) CH3CH2CH2Cl,AlCl3 (2) Br2,Fe 
C)     
D)     
E)  (1) (CH3) 2CHCl,AlCl3 (2) Br2,Fe" class="answers-bank-image d-inline" rel="preload" >
E)  (1) (CH3) 2CHCl,AlCl3 (2) Br2,FeF) A) and E)
G) B) and E)

Question 5

Which reagent(s) would you use to carry out the following transformation? ethylbenzene  →	o→  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. F) A) and E)
G) C) and D)

Question 6

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

Accepted Answer

A)  I
B)  II
C)  III
D)  IV
E)  VF) A) and D)
G) A) and B)

Question 7

Arrange the following compounds in order of decreasing reactivity in electrophilic substitution:  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" class="answers-bank-image d-inline" rel="preload" >

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 > IIIF) All of the above
G) C) and D)

Question 8

Which is the best sequence of reactions for the following transformation? 2; 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." class="answers-bank-image d-inline" rel="preload" >

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.F) B) and E)
G) A) and B)

Question 9

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 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,ROORF) B) and C)
G) C) and D)

Question 11

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.F) A) and D)
G) B) and D)

Question 12

What would be the major product of the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IV
E)  VF) B) and D)
G) All of the above

Question 13

What is the Birch reduction product of the following reaction?

Accepted Answer

A)  I
B)  II
C)  III
D)  IV
E)  VF) A) and E)
G) A) and D)

Question 14

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.F) B) and C)
G) A) and C)

Question 15

(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.F) None of the above
G) A) and C)

Question 16

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

Accepted Answer

A)  C6H5CH2CH3 + Br2,Fe3+  →	o→ 
B)  C6H5CH2CH3 + Br2,400 ∘\circ∘ C  →	o→ 
C)  C6H5CH2CH2OH + Br2,CCl4  →	o→ 
D)  C6H5CH=CH2 + HBr,ROOR  →	o→ 
E)  C6H5CH2CH3 + NBS,ROOR  →	o→F) D) and E)
G) C) and D)

Question 17

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.F) B) and C)
G) A) and E)

Question 18

What would be the product of the following reaction sequence?

Accepted Answer

A)  I
B)  II
C)  III
D)  IV
E)  VF) B) and C)
G) A) and B)

Question 19

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.F) A) and D)
G) A) and C)

Question 20

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)  VF) B) and E)
G) All of the above

Exam 15: Reactions of Aromatic Compounds

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

Correct AnswerverifiedShow Answer

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?

Correct AnswerverifiedThe 2 substitution product is favored si...View AnswerShow Answer

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

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What would be the product of the following reaction sequence?

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(Trifluoromethyl) benzene,C6H5CF3,will

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

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What would be the major product of the following reaction?

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

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

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

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What is the Birch reduction product of the following reaction?

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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?

Correct AnswerverifiedShow Answer

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

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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.

Correct AnswerverifiedThe major products are produced by bromi...View AnswerShow Answer

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

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

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

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

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

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

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

Correct Answer
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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?

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The 2 substitution product is favored si...
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(Trifluoromethyl) benzene,C₆H₅CF₃,will

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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?

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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.

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The major products are produced by bromi...
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