Deck 12: Reactions to Alkenes

Question 1

Based on your knowledge of the mechanisms involved,which of the reagents below would you expect to accomplish the following reaction? (Think through the mechanism!)

A) HBr
B) Br₂
C) PBr₃
D) NaBr
E) HBr + peroxides

Answer 1

Br₂

Question 2

Which reagents would you expect to accomplish the following transformation?

A) BH₃ then H₂O₂, ^-OH
B) Hg(O₂CCH₃)₂,
H₂O then NaBH₄
C) H₂O,H⁺
D) KMnO₄,H₂O,cold
E) cat.OsO₄,H₂O₂

Answer 2

Hg(O₂CCH₃)₂,
H₂O then NaBH₄

Question 3

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

A)

B)

C)

D)

E)

Answer 3

Question 4

What would be the product of the following reaction?

A)

B)

C)

D)

E)

Question 5

Radical polymerization of styrene produces what polymer? (n = large number)

A)

B)

C)

D)

E) None of the above.

Question 6

What would be the expected product of the following reaction?

A)

B)

C)

D)

E)

Question 7

What reagent(s)would accomplish the following reaction?

A) Br₂
B) NBS
C) Br₂ + light
D) Br₂ + FeBr₃
E) HBr

Question 8

What reagent(s)would accomplish the following transformation?

A) Br₂,h $\nu$
B) HBr
C) PBr₃
D) HBr + peroxides
E) HgBr₂ + NaBH₄

Question 9

Predict the major product of the following reaction:

A)

B)

C)

D)

E)

Question 10

Which of the reagents below would best accomplish the following transformation?

A) H₂O + cat.H₂SO₄
B) CH₃CO₃H,then NaOH + H₂O
C) Br₂ + H₂O
D) O₃ then Zn + HCl
E) KMnO₄ + ^-OH/ H₂O

Question 11

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

A)

B)

C)

D)

E)

Question 12

What reagents would be required to accomplish the following transformation?

A) KMnO₄, ^-OH,H₂O
B) BH₃ then H₂O₂
C) CH₃CO₃H then H₂O,H⁺
D) OsO₄,^tBuOOH,H₂O
E) Br₂,H₂O

Question 13

What type of reaction is the following?

A) elimination
B) addition
C) substitution
D) rearrangement
E) reduction

Question 14

What type of reaction is the following?

A) elimination
B) substitution
C) addition
D) rearrangement
E) reduction

Question 15

Considering the following reactions,you conclude that the stereochemistry of reactions #1 and #2 is:

A) anti and syn,respectively
B) syn and anti,respectively
C) anti and anti,respectively
D) syn and syn,respectively
E) None of the above.

Question 16

Polymerization reactions are thermodynamically favorable (exothermic)because

A) large molecules are more stable than small ones.
B) polymers precipitate,which shifts the equilibrium.
C) a sigma bond is more stable than a $\pi$ bond.
D) crosslinking stabilizes the product.
E) alkenes are too unstable to store.

Question 17

Reaction with ozone,followed by treatment with (CH₃)₂S,of which of the following would not yield any CH₃CHO?

A)

B)

C)

D)

E) Both B and D

Question 18

Which of the following reagents would best accomplish the following transformation?

A) NaBH₄
B) LiAlH₄
C) BH₃,NaBH₄
D) H₂SO₄
E) H₂,Pd

Question 19

Which of the following rearrangements would you not expect the cation below to undergo to any significant extent?

A)

B)

C)

D) None of the above would occur to a significant extent.
E) All of the above would be significant.

Question 20

What is the major product of the following reaction?

A)

B)

C)

D)

E)

Question 21

What is the major product of the following reaction?

A)

B)

C)

D) There is no reaction.
E)

Question 22

What reactant and product types would be most appropriate for the reagents shown?

A) alkene/Markovnikov alcohol
B) alkene/anti-Markovnikov alcohol
C) alkene/syn-1,2-diol
D) alkyne/anti-1,2-diol
E) alkene/epoxide

Question 23

Which of the following products is most likely to form under the reaction conditions?

A)

B)

C)

D)

E)

Question 24

What would be the expected product from the reaction shown?

A)

B)

C)

D)

E)

Question 25

Which of the following products is most likely to form under the reaction conditions?

A)

B)

C)

D)

E)

Question 26

Predict the product of the following reaction:

A)

B)

C)

D)

E) Equal amounts of A and B.

Question 27

Based on your knowledge of the mechanisms involved,which of the reagents below would you expect to accomplish the following reaction? (Think through the mechanism!)

A) H₂/Pd
B) Br₂
C) PBr₃
D) H₂SO₄
E) NaBH₄

Question 28

Which reagents would be appropriate for the chemical transformation shown below?

A) H₂O,H₂SO₄
B) BH₃,then H₂O₂, ^-OH
C) Hg(OAc)₂,H₂O,then NaBH₄
D) NaBH₄,CH₃OH
E) PCC

Question 29

Which of the following products is most likely to form under the reaction conditions?

A)

B)

C)

D)

E) None of the above.

Question 30

What reactant and product types would be most appropriate for the reagents shown?

A) alkene/alcohol
B) alkene/anti-1,2-diol
C) alkene/syn-1,2-diol
D) alkyne/ketone
E) alkyne/aldehyde

Question 31

Which of the following starting materials are most likely to give the product under the reaction conditions?

A)

B)

C)

D)

E)

Question 32

Predict the major product of the following reaction:

A)

B)

C)

D)

E)

Question 33

What is the best method to convert alkenes into alcohols following Markovnikov's Rule?

A) PCC
B) H₂O
C) hydroboration/oxidation
D) oxymercuration-demercuration
E) None of the above.

Question 34

Which reagents would be appropriate for the chemical transformation shown below?

A) H₂O,H₂SO₄
B) BH₃,then H₂O₂, ^-OH
C) Hg(OAc)₂,H₂O,then NaBH₄
D) NaBH₄,CH₃OH
E) PCC

Question 35

Which reagents would be appropriate for the chemical transformation shown below?

A) H₂O,H₂SO₄
B) BH₃,then H₂O₂, ^-OH
C) Hg(OAc)₂,H₂O,then NaBH₄
D) NaBH₄,CH₃OH
E) PCC

Question 36

How many products are possible in the reaction of trans-2-butene with Br₂?

A) 0
B) 1
C) 2
D) 3
E) 4

Question 37

What reactant and product types would be most appropriate for the reagents shown?

A) alkene/syn-1,2-diol
B) alkene/anti-1,2-diol
C) alkene/alcohol
D) alkene/aldehydes and/or ketones
E) alkene/epoxide

Question 38

What reactant and product types would be most appropriate for the reagents shown?

A) alkene/syn-1,2-dibromide
B) alkene/anti-1,2-dibromide
C) alkene/2-bromoalcohol
D) alkene/1,2-diol
E) alkene/epoxide

Question 39

What reactant and product types would be most appropriate for the reagents shown?

A) alkene/Markovnikov alcohol
B) alkene/anti-Markovnikov alcohol
C) alkene/1,2-diol
D) alkyne/1,2-diol
E) alcohol/alkene

Question 40

What reactant and product types would be most appropriate for the reagents shown?

A) alkene/Markovnikov alkyl bromide
B) alkene/anti-Markovnikov alkyl bromide
C) alkene/syn-1,2-dibromide
D) alkyne/anti-1,2-dibromide
E) alcohol/alkene

Question 41

What product,if any,would result from the reaction shown below?

A)

B)

C)

D) both A and B
E) no reaction occurs

Question 42

Select the product for the following reaction.

A)

B)

C)

D)

E) None of the above.

Question 43

Cholesterol is a major lipid component of atherosclerotic plaques and can be present at such high concentrations that it forms a crystalline phase within a diseased artery.In addition to cholesterol,the 5,6-secosterol compound has also been isolated.5,6-secostereol has been shown to be the product of an unforeseen oxidation reaction in the body.Which one of these reagents could be used convert cholesterol to the 5,6-secosterol? (Science 2003,302,1053)

A) K₂Cr₂O₇
B) O₃
C) (CH₃)₂S
D) HOOH
E) LiOH

Question 44

Select the major product of the olefin metathesis reaction ?

A)

B)

C)

D)

E)