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Predict the major product of the following Sandmeyer reaction: Predict the major product of the following Sandmeyer reaction: A) B) C) D) E)


A)
Predict the major product of the following Sandmeyer reaction: A) B) C) D) E)
B)
Predict the major product of the following Sandmeyer reaction: A) B) C) D) E)
C)
Predict the major product of the following Sandmeyer reaction: A) B) C) D) E)
D)
Predict the major product of the following Sandmeyer reaction: A) B) C) D) E)
E)
Predict the major product of the following Sandmeyer reaction: A) B) C) D) E)

F) B) and C)
G) C) and D)

Correct Answer

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How would you rank the following in decreasing order of reactivity toward nucleophilic aromatic substitution (most reactive on left) ? How would you rank the following in decreasing order of reactivity toward nucleophilic aromatic substitution (most reactive on left) ? A) 4 > 1 > 3 > 2 B) 2 > 3 > 1 > 4 C) 3 > 2 > 4 > 1 D) 1 > 3 > 2 > 4 E) impossible to predict


A) 4 > 1 > 3 > 2
B) 2 > 3 > 1 > 4
C) 3 > 2 > 4 > 1
D) 1 > 3 > 2 > 4
E) impossible to predict

F) A) and B)
G) None of the above

Correct Answer

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Starting with the labeled chlorobenzene (label indicated by *) ,what is the product of the following nucleophilic aromatic substitution reaction? Starting with the labeled chlorobenzene (label indicated by *) ,what is the product of the following nucleophilic aromatic substitution reaction? A) B) C) D) E) structures B and C


A)
Starting with the labeled chlorobenzene (label indicated by *) ,what is the product of the following nucleophilic aromatic substitution reaction? A) B) C) D) E) structures B and C
B)
Starting with the labeled chlorobenzene (label indicated by *) ,what is the product of the following nucleophilic aromatic substitution reaction? A) B) C) D) E) structures B and C
C)
Starting with the labeled chlorobenzene (label indicated by *) ,what is the product of the following nucleophilic aromatic substitution reaction? A) B) C) D) E) structures B and C
D)
Starting with the labeled chlorobenzene (label indicated by *) ,what is the product of the following nucleophilic aromatic substitution reaction? A) B) C) D) E) structures B and C
E) structures B and C

F) A) and D)
G) C) and E)

Correct Answer

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What would be the proper ranking of the following in order of decreasing acidity (most acidic on left) ? What would be the proper ranking of the following in order of decreasing acidity (most acidic on left) ? A) A > B > C B) B > C > A C) A > C > B D) B > A > C E) C > B > A


A) A > B > C
B) B > C > A
C) A > C > B
D) B > A > C
E) C > B > A

F) D) and E)
G) B) and D)

Correct Answer

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Arrange the following structures according to decreasing acidity? Arrange the following structures according to decreasing acidity? A) 1 > 3 > 4 > 2 B) 2 > 4 > 3 > 1 C) 4 > 3 > 1 > 2 D) 3 > 2 > 1 > 4 E) 4 > 1 > 3 > 2


A) 1 > 3 > 4 > 2
B) 2 > 4 > 3 > 1
C) 4 > 3 > 1 > 2
D) 3 > 2 > 1 > 4
E) 4 > 1 > 3 > 2

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

Correct Answer

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C

What happens when a secondary amine is treated with nitrous acid?


A) A diazonium salt is formed.
B) It immediately loses nitrogen to form a carbocation.
C) A simple acid-base reaction occurs to give an alkyl ammonium nitrite salt.
D) An N-nitroso amine is formed.
E) A dealkylation occurs to give a primary amine.

F) A) and D)
G) B) and C)

Correct Answer

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Which of the following is not a valid resonance contributor to the benzyl radical?


A)
Which of the following is not a valid resonance contributor to the benzyl radical? A) B) C) D) E)
B)
Which of the following is not a valid resonance contributor to the benzyl radical? A) B) C) D) E)
C)
Which of the following is not a valid resonance contributor to the benzyl radical? A) B) C) D) E)
D)
Which of the following is not a valid resonance contributor to the benzyl radical? A) B) C) D) E)
E)
Which of the following is not a valid resonance contributor to the benzyl radical? A) B) C) D) E)

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

Correct Answer

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By which of the following can the N2 group of a benzenediazonium salt not be substituted? By which of the following can the N<sub>2</sub> group of a benzenediazonium salt not be substituted? A) CN B) CH<sub>3</sub> C) H D) F E) OH


A) CN
B) CH3
C) H
D) F
E) OH

F) A) and D)
G) D) and E)

Correct Answer

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What is the main use of azo compounds in general? What is the main use of azo compounds in general? A) Antibiotic properties B) Fragrances and flavorings C) Chemotherapy agents D) Herbicides and/or pesticides E) Dyes and coloring agents


A) Antibiotic properties
B) Fragrances and flavorings
C) Chemotherapy agents
D) Herbicides and/or pesticides
E) Dyes and coloring agents

F) A) and B)
G) C) and D)

Correct Answer

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The following reaction most likely proceeds by what mechanism: The following reaction most likely proceeds by what mechanism: A) S<sub>N</sub>2 B) S<sub>N</sub>1 C) E2 D) E1 E) Free radical halogenation


A) SN2
B) SN1
C) E2
D) E1
E) Free radical halogenation

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

Correct Answer

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When considering the mechanism of the reaction shown below,which of the following is most likely an intermediate along the reaction pathway? When considering the mechanism of the reaction shown below,which of the following is most likely an intermediate along the reaction pathway? A) B) C) D) E)


A)
When considering the mechanism of the reaction shown below,which of the following is most likely an intermediate along the reaction pathway? A) B) C) D) E)
B)
When considering the mechanism of the reaction shown below,which of the following is most likely an intermediate along the reaction pathway? A) B) C) D) E)
C)
When considering the mechanism of the reaction shown below,which of the following is most likely an intermediate along the reaction pathway? A) B) C) D) E)
D)
When considering the mechanism of the reaction shown below,which of the following is most likely an intermediate along the reaction pathway? A) B) C) D) E)
E)
When considering the mechanism of the reaction shown below,which of the following is most likely an intermediate along the reaction pathway? A) B) C) D) E)

F) B) and E)
G) B) and C)

Correct Answer

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E

Which ion would be most stabilized by resonance?


A)
Which ion would be most stabilized by resonance? A) B) C) D) E) All are equally stabilized.
B)
Which ion would be most stabilized by resonance? A) B) C) D) E) All are equally stabilized.
C)
Which ion would be most stabilized by resonance? A) B) C) D) E) All are equally stabilized.
D)
Which ion would be most stabilized by resonance? A) B) C) D) E) All are equally stabilized.
E) All are equally stabilized.

F) All of the above
G) C) and D)

Correct Answer

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What material is produced easily by means of the Kolbe reaction? (sodium phenoxide + CO2 + heat/pressure,then H3O+)


A) Phenol
B) Benzaldehyde
C) Succinic acid
D) Cinnamic acid
E) Salicylic acid

F) A) and E)
G) C) and D)

Correct Answer

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E

Which of the following resonance structures of the phenoxide anion would be the major contributor to the real structure?


A)
Which of the following resonance structures of the phenoxide anion would be the major contributor to the real structure? A) B) C) D) E) All are equally important.
B)
Which of the following resonance structures of the phenoxide anion would be the major contributor to the real structure? A) B) C) D) E) All are equally important.
C)
Which of the following resonance structures of the phenoxide anion would be the major contributor to the real structure? A) B) C) D) E) All are equally important.
D)
Which of the following resonance structures of the phenoxide anion would be the major contributor to the real structure? A) B) C) D) E) All are equally important.
E) All are equally important.

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

Correct Answer

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Which of the following represents a hydrogenolysis reaction?


A)
Which of the following represents a hydrogenolysis reaction? A) B) C) D) E) Two or more of these are correct.
B)
Which of the following represents a hydrogenolysis reaction? A) B) C) D) E) Two or more of these are correct.
C)
Which of the following represents a hydrogenolysis reaction? A) B) C) D) E) Two or more of these are correct.
D)
Which of the following represents a hydrogenolysis reaction? A) B) C) D) E) Two or more of these are correct.
E) Two or more of these are correct.

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

Correct Answer

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Which of the reagents given below would accomplish the reaction shown? Which of the reagents given below would accomplish the reaction shown? A) H<sub>2</sub>O<sub>2</sub>,KOH,heat B) Na<sub>2</sub>Cr<sub>2</sub>O<sub>7</sub>,H<sup>+</sup>,heat C) ClCO<sub>2</sub>H,AlCl<sub>3</sub> D) O<sub>3</sub>,then H<sub>2</sub>O E) None of these.


A) H2O2,KOH,heat
B) Na2Cr2O7,H+,heat
C) ClCO2H,AlCl3
D) O3,then H2O
E) None of these.

F) A) and B)
G) C) and D)

Correct Answer

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Why does the substitution of ortho or para nitro groups onto chlorobenzene greatly increase the tendency of the chlorine to be displaced by nucleophiles?


A) NO2 groups stabilize the SN1 transition state by resonance.
B) The NO2 groups facilitate removal of a hydrogen to chlorine.
C) NO2 groups stabilize the SN2 transition state.
D) NO2 groups stabilize negative charge resulting from addition of a nucleophile.
E) The NO2 groups exert a general inductive effect which is independent of substitution position.

F) B) and C)
G) B) and E)

Correct Answer

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What would be the result of the following? What would be the result of the following? A) <sup> </sup> B) C) D) E) no reaction


A)
What would be the result of the following? A) <sup> </sup> B) C) D) E) no reaction
B)
What would be the result of the following? A) <sup> </sup> B) C) D) E) no reaction
C)
What would be the result of the following? A) <sup> </sup> B) C) D) E) no reaction
D)
What would be the result of the following? A) <sup> </sup> B) C) D) E) no reaction
E) no reaction

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

Correct Answer

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What would be the expected product(s) from the following reaction? What would be the expected product(s) from the following reaction? A) <sup> </sup> B) C) D) both A and B E) All of the above.


A)
What would be the expected product(s) from the following reaction? A) <sup> </sup> B) C) D) both A and B E) All of the above.
B)
What would be the expected product(s) from the following reaction? A) <sup> </sup> B) C) D) both A and B E) All of the above.
C)
What would be the expected product(s) from the following reaction? A) <sup> </sup> B) C) D) both A and B E) All of the above.
D) both A and B
E) All of the above.

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

Correct Answer

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Predict the major product of the following reaction: Predict the major product of the following reaction: A) B) C) D) E)


A)
Predict the major product of the following reaction: A) B) C) D) E)
B)
Predict the major product of the following reaction: A) B) C) D) E)
C)
Predict the major product of the following reaction: A) B) C) D) E)
D)
Predict the major product of the following reaction: A) B) C) D) E)
E)
Predict the major product of the following reaction: A) B) C) D) E)

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

Correct Answer

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