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Rank the following carbocations according to their increasing stability. Rank the following carbocations according to their increasing stability. A) A<B<C<D B) A<C<B<D C) C<A<B<D D) A<C<D<B E) None of the above.


A) A<B<C<D
B) A<C<B<D
C) C<A<B<D
D) A<C<D<B
E) None of the above.

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The major product of the following reaction conditions will result from: The major product of the following reaction conditions will result from: A) S<sub>N</sub>2 B) S<sub>N</sub>1 C) E2 D) E1 E) there is no way to know


A) SN2
B) SN1
C) E2
D) E1
E) there is no way to know

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B

If the concentration of NaOH is doubled in the following reaction,what will happen to the reaction rate? If the concentration of NaOH is doubled in the following reaction,what will happen to the reaction rate? A) no change B) double C) quadruple D) cut in half E) None of the above.


A) no change
B) double
C) quadruple
D) cut in half
E) None of the above.

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Solvolysis of 2-bromo-2-methylpropane occurs through what mechanism?


A) SN2
B) E1
C) E2
D) SN1
E) A and C

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For the transformation of norepinephrine to epinephrine (adrenaline) ,what is the likely mechanism? For the transformation of norepinephrine to epinephrine (adrenaline) ,what is the likely mechanism? A) S<sub>N</sub>1 B) S<sub>N</sub>2 C) E1 D) E2 E) both A and B are likely


A) SN1
B) SN2
C) E1
D) E2
E) both A and B are likely

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Rank the following according to their increasing reactivity with water. Rank the following according to their increasing reactivity with water. A) CH<sub>3</sub>Br < CH<sub>3</sub>CH<sub>2</sub>Br < (CH<sub>3</sub>) <sub>3</sub>CBr < ( CH<sub>3</sub>) <sub>2</sub>CHBr B) CH<sub>3</sub>Br < CH<sub>3</sub>CH<sub>2</sub>Br < ( CH<sub>3</sub>) <sub>2</sub>CHBr < (CH<sub>3</sub>) <sub>3</sub>CBr C) (CH<sub>3</sub>) <sub>3</sub>CBr < ( CH<sub>3</sub>) <sub>2</sub>CHBr < CH<sub>3</sub>CH<sub>2</sub>Br < CH<sub>3</sub>Br D) All of these will react with water at the same rate. E) None of the above will react with water.


A) CH3Br < CH3CH2Br < (CH3) 3CBr < ( CH3) 2CHBr
B) CH3Br < CH3CH2Br < ( CH3) 2CHBr < (CH3) 3CBr
C) (CH3) 3CBr < ( CH3) 2CHBr < CH3CH2Br < CH3Br
D) All of these will react with water at the same rate.
E) None of the above will react with water.

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What would be the major organic product of the following reaction? What would be the major organic product of the following reaction? A) <sup> </sup> B) C) D) E)


A)
What would be the major organic product of the following reaction? A) <sup> </sup> B) C) D) E)
B)
What would be the major organic product of the following reaction? A) <sup> </sup> B) C) D) E)
C)
What would be the major organic product of the following reaction? A) <sup> </sup> B) C) D) E)
D)
What would be the major organic product of the following reaction? A) <sup> </sup> B) C) D) E)
E)
What would be the major organic product of the following reaction? A) <sup> </sup> B) C) D) E)

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D

For the transformation below,give the structure of the starting material. For the transformation below,give the structure of the starting material. A) B) C) D) E)


A)
For the transformation below,give the structure of the starting material. A) B) C) D) E)
B)
For the transformation below,give the structure of the starting material. A) B) C) D) E)
C)
For the transformation below,give the structure of the starting material. A) B) C) D) E)
D)
For the transformation below,give the structure of the starting material. A) B) C) D) E)
E)
For the transformation below,give the structure of the starting material. A) B) C) D) E)

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(S) -1-bromo-1-fluoroethane reacts with NaOMe to give: (S) -1-bromo-1-fluoroethane reacts with NaOMe to give: A) <sup> </sup> B) C) CH<sub>3</sub>CHFOCH<sub>3</sub> D) CH<sub>3</sub>CHBrOCH<sub>3</sub> E) CH<sub>3</sub>CH(OCH<sub>3</sub>) <sub>2</sub>


A)
(S) -1-bromo-1-fluoroethane reacts with NaOMe to give: A) <sup> </sup> B) C) CH<sub>3</sub>CHFOCH<sub>3</sub> D) CH<sub>3</sub>CHBrOCH<sub>3</sub> E) CH<sub>3</sub>CH(OCH<sub>3</sub>) <sub>2</sub>
B)
(S) -1-bromo-1-fluoroethane reacts with NaOMe to give: A) <sup> </sup> B) C) CH<sub>3</sub>CHFOCH<sub>3</sub> D) CH<sub>3</sub>CHBrOCH<sub>3</sub> E) CH<sub>3</sub>CH(OCH<sub>3</sub>) <sub>2</sub>
C) CH3CHFOCH3
D) CH3CHBrOCH3
E) CH3CH(OCH3) 2

Correct Answer

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To which side,if any,would the following equilibrium lie? (Do not consider any further reactions here.) To which side,if any,would the following equilibrium lie? (Do not consider any further reactions here.) A) to the left B) to the right C) equally to the right and left D) there is no way to tell E) this reaction cannot occur at all


A) to the left
B) to the right
C) equally to the right and left
D) there is no way to tell
E) this reaction cannot occur at all

Correct Answer

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


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

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Which of the following is the least nucleophilic base?


A) (CH3CH2) 3N
B)
Which of the following is the least nucleophilic base? A) (CH<sub>3</sub>CH<sub>2</sub>) <sub>3</sub>N B) C) D) E)
C)
Which of the following is the least nucleophilic base? A) (CH<sub>3</sub>CH<sub>2</sub>) <sub>3</sub>N B) C) D) E)
D)
Which of the following is the least nucleophilic base? A) (CH<sub>3</sub>CH<sub>2</sub>) <sub>3</sub>N B) C) D) E)
E)
Which of the following is the least nucleophilic base? A) (CH<sub>3</sub>CH<sub>2</sub>) <sub>3</sub>N B) C) D) E)

Correct Answer

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For the transformation below,give the structure of the starting material. For the transformation below,give the structure of the starting material. A) B) C) D) E) Both B and C will provide the product shown.


A)
For the transformation below,give the structure of the starting material. A) B) C) D) E) Both B and C will provide the product shown.
B)
For the transformation below,give the structure of the starting material. A) B) C) D) E) Both B and C will provide the product shown.
C)
For the transformation below,give the structure of the starting material. A) B) C) D) E) Both B and C will provide the product shown.
D)
For the transformation below,give the structure of the starting material. A) B) C) D) E) Both B and C will provide the product shown.
E) Both B and C will provide the product shown.

Correct Answer

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Which mechanism proceeds with inversion of configuration?


A) bimolecular elimination (E2)
B) unimolecular elimination (E1)
C) unimolecular substitution (SN1)
D) bimolecular substitution (SN2)
E) free-radical halogenation

Correct Answer

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D

Indicate the expected major product of the following reaction: Indicate the expected major product of the following reaction: A) <sup> </sup> B) C) D) E)


A)
Indicate the expected major product of the following reaction: A) <sup> </sup> B) C) D) E)
B)
Indicate the expected major product of the following reaction: A) <sup> </sup> B) C) D) E)
C)
Indicate the expected major product of the following reaction: A) <sup> </sup> B) C) D) E)
D)
Indicate the expected major product of the following reaction: A) <sup> </sup> B) C) D) E)
E)
Indicate the expected major product of the following reaction: A) <sup> </sup> B) C) D) E)

Correct Answer

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Predict the product of reaction of the following deuterated compound. Predict the product of reaction of the following deuterated compound. A) B) C) D) E)


A)
Predict the product of reaction of the following deuterated compound. A) B) C) D) E)
B)
Predict the product of reaction of the following deuterated compound. A) B) C) D) E)
C)
Predict the product of reaction of the following deuterated compound. A) B) C) D) E)
D)
Predict the product of reaction of the following deuterated compound. A) B) C) D) E)
E)
Predict the product of reaction of the following deuterated compound. A) B) C) D) E)

Correct Answer

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Which would be true of the following reactions? Which would be true of the following reactions? A) cis would react faster B) trans would react faster C) cis and trans would react at the same rates D) no reaction is expected under these conditions E) the product shown would not be formed


A) cis would react faster
B) trans would react faster
C) cis and trans would react at the same rates
D) no reaction is expected under these conditions
E) the product shown would not be formed

Correct Answer

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Predict the major product of the following SN1 reaction: Predict the major product of the following S<sub>N</sub>1 reaction: A) B) C) D) E)


A)
Predict the major product of the following S<sub>N</sub>1 reaction: A) B) C) D) E)
B)
Predict the major product of the following S<sub>N</sub>1 reaction: A) B) C) D) E)
C)
Predict the major product of the following S<sub>N</sub>1 reaction: A) B) C) D) E)
D)
Predict the major product of the following S<sub>N</sub>1 reaction: A) B) C) D) E)
E)
Predict the major product of the following S<sub>N</sub>1 reaction: A) B) C) D) E)

Correct Answer

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Which of the following molecules will readily undergo an elimination reaction when treated with NaOCH3?


A)
Which of the following molecules will readily undergo an elimination reaction when treated with NaOCH<sub>3</sub>? A) B) C) D) E) None of the above.
B)
Which of the following molecules will readily undergo an elimination reaction when treated with NaOCH<sub>3</sub>? A) B) C) D) E) None of the above.
C)
Which of the following molecules will readily undergo an elimination reaction when treated with NaOCH<sub>3</sub>? A) B) C) D) E) None of the above.
D)
Which of the following molecules will readily undergo an elimination reaction when treated with NaOCH<sub>3</sub>? A) B) C) D) E) None of the above.
E) None of the above.

Correct Answer

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Which one of the following would undergo E2 elimination most rapidly?


A)
Which one of the following would undergo E2 elimination most rapidly? A) B) C) D) E) All would react at the same rate.
B)
Which one of the following would undergo E2 elimination most rapidly? A) B) C) D) E) All would react at the same rate.
C)
Which one of the following would undergo E2 elimination most rapidly? A) B) C) D) E) All would react at the same rate.
D)
Which one of the following would undergo E2 elimination most rapidly? A) B) C) D) E) All would react at the same rate.
E) All would react at the same rate.

Correct Answer

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