Deck 7: Further Reactions of Haloalkanes: Unimolecular Substitution and Pathways of Elimination

Question 1

Indicate the expected major product of the following reaction:

A)

B)

C)

D)

E)

Answer 1

Question 2

Which of the cyclohexyl bromides would you expect to react the fastest in the following reaction?

A)

B)

C)

D)

E) All would react at the same rate.

Answer 2

Question 3

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

A)

B)

C)

D)

E) None of the above.

Answer 3

Question 4

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

Question 5

Which of the bases below would be best to accomplish the following reaction?

A) CH₃O^- Na⁺
B) CH₃CH₂O^- Na⁺
C) (CH₃)₂CHO^- Na⁺
D) (CH₃)₃CO^- Na⁺
E) Na^{+ -}OH

Question 6

(S)-1-bromo-1-fluoroethane reacts with NaOMe to give:

A)

B)

C) CH₃CHFOCH₃
D) CH₃CHBrOCH₃
E) CH₃CH(OCH₃)₂

Question 7

Which of the following is the least nucleophilic base?

A) (CH₃CH₂)₃N
B)

C)

D)

E)

Question 8

Which mechanism proceeds with inversion of configuration?

A) bimolecular elimination (E2)
B) unimolecular elimination (E1)
C) unimolecular substitution (S_N1)
D) bimolecular substitution (S_N2)
E) free-radical halogenation

Question 9

Predict the major product of the following reaction:

A)
only
B)

C)
only
D)

E)
and

Question 10

How many alkene products are possible in the following reaction?

A) None; cannot eliminate
B) One
C) Two
D) Three
E) Four

Question 11

Predict the product of reaction of the following deuterated compound.

A)

B)

C)

D)

E)

Question 12

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

Question 13

The major product of the following reaction conditions will result from:

A) S_N2
B) S_N1
C) E2
D) E1
E) there is no way to know

Question 14

What would be the major organic product of the following reaction?

A)

B)

C)

D)

E)

Question 15

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

A) S_N2
B) E1
C) E2
D) S_N1
E) A and C

Question 16

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.

Question 17

Which of the haloalkanes below would you expect to most rapidly undergo the reaction shown?

A) CH₃CH₂Br
B) CH₃Br
C) (CH₃)₃CBr
D) CH₃CHBrCH₃
E)

Question 18

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

A)

B)

C)

D)

E) All would react at the same rate.

Question 19

Predict the major product of the following S_N1 reaction:

A)

B)

C)

D)

E)

Question 20

Which of the nucleophiles shown below would not cause an E2 elimination as the predominant reaction?

A) NaNH₂
B) CH₃CH₂OH
C) (^-CN)
D) (^-OH)
E) CH₃O^-

Question 21

Rank the following carbocations according to their increasing stability.

A) AB) AC) CD) AE) None of the above.

Question 22

For the transformation of norepinephrine to epinephrine (adrenaline),what is the likely mechanism?

A) S_N1
B) S_N2
C) E1
D) E2
E) both A and B are likely

Question 23

For the transformation below,give the structure of the starting material.

A)

B)

C)

D)

E)

Question 24

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.

Question 25

Rank the following according to their increasing reactivity 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.