Deck 6: Reactions of Alkenes

Question 1

Which statement(s)are true according to the Hammond postulate?

A)In an exergonic reaction, the transition state is more similar in energy to the reactant than the product.
B)In an exergonic reaction, the transition state is more similar in energy to the product than the reactant.
C)In an endergonic reaction, the transition state is more similar in energy to the reactant than the product.
D)In an endergonic reaction, the transition state is more similar in energy to the product than the reactant.
E)A and D

Answer 1

A and D

Question 2

Draw the major organic product generated in the reaction below.

Answer 2

Question 3

Which of the following alkenes reacts with HCl at the slowest rate?

A)
B)
C)
D)
E)

Answer 3

Question 4

Draw the major organic product generated in the reaction below.

Question 5

Complete the following reaction and provide a detailed, step-by-step mechanism for the process.

Question 6

Identify the most stable carbocation.

A)
B)
C)
D)
E)

Question 7

What is hyperconjugation, and how does it affect carbocation stability?

Question 8

Which of the following is the most stable carbocation?

A)I
B)II
C)III
D)IV
E)V

Question 9

Provide the structure of the major organic product in the reaction below.

Question 10

For an endergonic reaction step, the Hammond postulate allows one to say that ________.

A)the transition state of the step resembles the reactants of the step
B)the transition state of the step resembles the products of the step
C)the step is rate-determining since it has the smallest E_a
D)the reaction containing this step is overall first order
E)the transition state is precisely symmetric with bond-breaking and bond-forming occurring to the same extent

Question 11

Provide the structure of the major organic product in the reaction below.

Question 12

Which of the following compounds will react most rapidly with HCl?

A)5-methyl-1-hexene
B)4-methyl-1-hexene
C)(E)-5-methyl-2-hexene
D)(E)-2-methyl-3-hexene
E)2-methyl-2-hexene

Question 13

Draw the major organic product generated in the reaction below.

Question 14

Draw the product.

Question 15

Draw the major organic product generated in the reaction below.

Question 16

Draw the major organic product generated in the reaction below.

Question 17

Draw the major organic product generated in the reaction below.

Question 18

According to the Hammond Postulate, which of the following is correct?

A)The transition state of an endothermic reaction step will be more reactant-like than product-like.
B)The intermediate of an endothermic reaction step will be more reactant-like than product-like.
C)The transition state of an exothermic reaction step will be more reactant-like than product-like.
D)All transition states are more product-like than reactant-like.
E)All transition states are more reactant-like than product-like.

Question 19

Which alkene reacts the fastest with HBr?

A)
B)
C)
D)
E)

Question 20

Based on the relative stabilities of the intermediates involved, explain the basis for Markovnikov's rule in the addition of hydrogen halides to alkenes.

Question 21

Identify the true statements in the mechanism in the addition of water to an alkene.

A)The addition of the electrophile is a slow step.
B)The addition of the nucleophile is a fast step.
C)A carbocation is formed as an intermediate.
D)Water abstracts the extra proton from the protonated alcohol.
E)All of the above

Question 22

Provide the major organic product(s)in the reaction below.

Question 23

Provide the structure of the major organic product in the reaction below.

Question 24

Provide the structure of the major organic product of the following reaction.

Question 25

Give the product for the reaction of 1-butene with methanol in the presence of acid.

A)1-ethoxybutane
B)2-ethoxybutane
C)1-methoxybutane
D)2-methoxybutane
E)1-butanol

Question 26

Draw the product.

Question 27

Which is more highly regioselective the addition of HCl to methylenecyclohexane or to 1-methylcyclohexene? Explain.

Question 28

Provide the structure of the major organic product of the following reaction.

Question 29

Draw the product.

Question 30

Draw the major organic product generated in the reaction below.

Question 31

Provide the major organic product(s)in the reaction below.

Question 32

Which of the following alkenes yield(s)3-bromo-3-methylpentane as the major product upon addition of HBr?

A)I and II only
B)III only
C)I, II, nad III only
D)all of them
E)none of them

Question 33

Draw the major organic product generated in the reaction below.

Question 34

Draw the major organic product generated in the reaction below.

Question 35

Complete the following reaction and provide a detailed, step-by-step mechanism for the process.

Question 36

Provide the structure of the major organic product in the reaction below.

Question 37

What is the major product of the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 38

What is the major product from the acid-catalyzed hydration of 2-methyl-2-pentene?

A)2-methylpentane
B)2-methyl-1-pentanol
C)2-methyl-2-pentanol
D)2-methyl-3-pentanol
E)1-methoxypentane

Question 39

Draw the structures of the two alkenes that react with HBr to yield 1-bromo-1-methylcyclopentane as the major organic product.

Question 40

Propose a mechanism for the following reaction:

Question 41

Give the major organic product of the reaction shown.

A)
B)
C)
D)
E)

Question 42

Provide the major organic product(s)in the reaction below.

Question 43

Which of the following is the best reaction sequence to use if one wants to accomplish a Markovnikov addition of water to an alkene with minimal skeletal rearrangement?

A)water + dilute acid
B)water + concentrated acid
C)oxymercuration-demercuration
D)hydroboration-oxidation
E)none of the above

Question 44

Provide the structure of the major organic product of the following reaction.

Question 45

Provide the structure of the major organic product in the reaction below.

Question 46

Draw the major organic product generated in the reaction below.

Question 47

Give the best product for the following reaction.

A)
B)
C)
D)
E)

Question 48

Which statement is true in the oxymercuration-reduction of an alkene?

A)Markovnikov orientation and syn addition occur.
B)Markovnikov orientation and anti addition occur.
C)Anti-Markovnikov orientation and syn addition occur.
D)Anti-Markovnikov orientation and anti addition occur.
E)Markonikov orientation and both syn and anti addition occur.

Question 49

What reagents are needed to accomplish the following transformation?

A)H₂O/H⁺
B)H₂O/Peroxide
C)OH^-
D)BH₃
E)1) BH₃/ 2. HO^-, H₂O₂, H₂O

Question 50

Provide the major organic product(s)in the reaction below.

Question 51

Draw the product.

Question 52

Which of the following carbocations is likely to rearrange?

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

Question 53

What is the name of the major organic product of the following reaction?

A)3,3-dimethyl-1-butanol
B)3,3-dimethyl-2-butanol
C)2,3-dimethyl-2-butanol
D)2,3-dimethyl-1-butanol
E)4-methyl-2-pentanol

Question 54

Provide the major organic product in the reaction below.

A)
B)
C)
D)
E)

Question 55

Provide the structure of the major organic product in the reaction below.

Question 56

What reagents can best be used to accomplish the following transformation?

A)1) BH₃∙THF 2. HO^-, H₂O₂
B)H⁺, H₂O
C)1) Hg(OAc)₂, H₂O/THF 2. NaBH₄
D)1) Hg(O₂CCF₃)₂, CH₃OH 2. NaBH₄
E)NaOH, H₂O

Question 57

Draw the major organic product generated in the reaction below.

Question 58

Which statement is true in the hydroboration-oxidation of an alkene?

A)Markovnikov orientation and syn addition occur.
B)Markovnikov orientation and anti addition occur.
C)Anti-Markovnikov orientation and syn addition occur.
D)Anti-Markovnikov orientation and anti addition occur.
E)Markovnikov orientation and both syn and anti addition occur.

Question 59

Provide the major organic product(s)in the reaction below.

Question 60

Provide the structure of the major organic product of the following reaction.

Question 61

Draw the product.

Question 62

Provide the major organic product(s)in the reaction below.

Question 63

Provide a detailed, step-by-step mechanism for the reaction shown below.

Question 64

Give the intermediate for the halohydrin reaction.

A)a halonium ion
B)the most stable carbocation with OH on the adjacent carbon
C)the most stable carbocation with X on the adjacent carbon
D)a cyclic oxonium ion
E)the most stable carbanion

Question 65

Provide the structure of the major organic product in the reaction below.

Question 66

Draw the major organic product generated in the reaction below.

Question 67

Draw the structure of the major product of the reaction below.

Question 68

Which reaction intermediate is formed when Br₂/CCl₄ reacts with cyclohexene?

A)I
B)II
C)III
D)IV
E)V

Question 69

Draw the major organic product generated in the reaction below.

Question 70

Draw the products.

Question 71

Provide the structure of the major organic product in the reaction below.

Question 72

Give the product for the reaction that occurs when 1-pentene is treated with Cl₂.

A)1-chloropentane
B)2-chloropentane
C)1,1-dichloropentane
D)2,2-dichloropentane
E)1,2-dichloropentane

Question 73

Complete the following reaction and provide a detailed, step-by-step mechanism for the process.

Question 74

Provide the major organic product(s)in the reaction below.

Question 75

What is the major product of the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 76

Draw the major organic product generated in the reaction below.

Question 77

Draw the major organic product generated in the reaction below.

Question 78

Provide the major organic product in the reaction below.

A)
B)
C)
D)
E)

Question 79

Provide the structure of the major organic product in the reaction below.

Question 80

Provide the major organic product(s)in the reaction below.