Deck 11: Reactions of Alcohols, Ethers, Epoxides, and Sulfur-Containing Compounds

Question 1

Name and provide the structure of the major organic product which results when (R)-3,3-dimethyl-2-butanol is heated in the presence of HBr.

Answer 1

2-bromo-2,3-dimethylbutane

Question 2

Provide the major organic product of the reaction below.

Answer 2

Question 3

Provide the major organic product of the reaction below.

Answer 3

Question 4

When 1-pentanol is heated with HCl/ZnCl₂, 1-chloropentane is the major organic product. This reaction proceeds through an ________ mechanism, and ________ is produced as a byproduct.

A)S_N1, H₂O
B)S_N2, H₂O
C)S_N1, H₂
D)S_N2, H₂
E)E2, H₂

Question 5

Give the major organic product for the following reaction.

A)
B)
C)
D)
E)no reaction

Question 6

Propose a mechanism for the following reaction:

Question 7

Provide the major organic product of the reaction below.

Question 8

Which of the following alcohols will react most rapidly with the Lucas reagent (HCl, ZnCl₂)?

A)(CH₃)₃COH
B)CH₃CH₂CH₂CH₂OH
C)CH₃CHOHCH₂CH₃
D)(CH₃)₂CHCH₂OH

Question 9

Which of the following is the best method for preparing CH₃Br?

A)CH₃OH + Br^-
B)CH₃OH + HBr
C)CH₃OH + Br₂
D)CH₃OH + NaBr
E)CH₃OH + Br⁺

Question 10

What is the major product of the following reaction?

A)
B)
C)
D)
E)

Question 11

Why are alcohols typically poor electrophiles?

Question 12

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

Question 13

Give the major organic product for the following reaction.

A)
B)
C)
D)
E)no reaction

Question 14

Give the major organic product for the following reaction.

A)
B)
C)
D)
E)no reaction

Question 15

What is the major product of the following reaction?

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

Question 16

Provide the major organic product of the reaction below.

Question 17

Predict the major product of the reaction below and provide a stepwise mechanism which accounts for its formation.
CH₃(CH₂)₆CH₂OH + HBr →

Question 18

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

Question 19

Provide the major organic product of the reaction below.

Question 20

A compound (A)C₄H₁₀O is optically active. (A)reacts with HCl and ZnCl₂ (Lucas test)to form a cloudy product within 10 minutes. Deduce the structure of (A).

Question 21

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

Question 22

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

Question 23

Provide the structure of the major organic product in the reaction below.
(CH₃)₂CHCH₂OH

Question 24

Give the major organic product for the following reaction.

A)
B)
C)
D)
E)no reaction

Question 25

What is the product of the following reaction?

A)
B)
C)
D)
E)

Question 26

Provide the major organic product of the reaction below.

Question 27

When (R)-2-butanol is treated with TsCl in pyridine, the product formed is ________.

A)an achiral compound
B)a mixture of diastereomers
C)a racemic mixture
D)a single enantiomer
E)none of the above

Question 28

Provide the major organic product of the reaction below.

Question 29

Which of the following reagents is best used in the conversion of methyl alcohol to methyl chloride?

A)Cl₂/CCl₄
B)Cl₂/hυ
C)Cl^-
D)SOCl₂
E)NaCl

Question 30

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

Question 31

Draw the tosylate ion and explain why it is a particularly good leaving group.

Question 32

Provide the major organic product of the reaction below.

Question 33

What is the product of the following reaction?

A)
B)
C)
D)
E)

Question 34

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

Question 35

What is the major product of the following reaction?

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

Question 36

Give the major organic product for the following reaction.

A)
B)
C)
D)
E)

Question 37

Provide the structure of the major organic product of the following reaction. Explain the stereochemistry which results in this product.

Question 38

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

Question 39

Give the major product for the following reaction.

Question 40

Provide the major organic product of the reaction below.

Question 41

Draw all likely products of the following reaction and circle the product you expect to predominate.

Question 42

Draw all likely products of the following reaction and circle the product you expect to predominate.

Question 43

Starting with isopropyl alcohol as the only organic material, synthesize isopropyl propyl ether.

Question 44

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

Question 45

Which of the following alcohols dehydrates with the fastest rate?

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

Question 46

What is the major product of the following reaction?

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

Question 47

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

Question 48

Give the major product for the following reaction.

A)
B)
C)
D)
E)

Question 49

Give the major product for the following reaction.

A)
B)
C)
D)
E)

Question 50

Draw all likely products of the following reaction and circle the product you expect to predominate.
2-pentanol

Question 51

Provide the major organic product of the reaction below.

Question 52

Provide the major organic product of the reaction below.

Question 53

Which of the following is least likely to be found in the product mixture which results when 2,2-dimethyl-3-pentanol is heated in phosphoric acid?

A)(E)-4, 4-dimethyl-2-pentene
B)(Z)-4, 4-dimethyl-2-pentene
C)2, 3-dimethyl-2-pentene
D)2, 3-dimethyl-1-pentene
E)4, 4-dimethyl-1-pentene

Question 54

Provide the major organic product of the reaction below.

Question 55

Which of the following alcohols gives a rearranged carbocation when dehydrated?

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

Question 56

What is the product of the following reaction?

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

Question 57

Provide the major organic product of the reaction below.

Question 58

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

Question 59

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

Question 60

Which of the following alcohols, when heated with H₂SO₄, will undergo dehydration more rapidly? Explain.

Question 61

What is/are the product(s)from the following reaction?

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

Question 62

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

Question 63

Provide the major organic product of the reaction below.

Question 64

Provide the major organic product in the reaction below.

Question 65

When dipentyl ether is treated with excess HI, through what type of mechanism(s)does the major product result?

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

Question 66

What are the major products from the following reaction?

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

Question 67

Propose a mechanism for the following reaction:

Question 68

Give the major organic product for the following reaction.

A)CH₃I
B)CH₃CH₂I
C)
D)CH₃CH₂CH₂CH₂I
E)CH₃CH₂CH₂I

Question 69

What is the major product for the following reaction?

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

Question 70

Give the major product for the following reaction.

A)
B)
C)
D)
E)no reaction

Question 71

Give the major product for the following reaction.

A)
B)
C)
D)
E)

Question 72

What is the major product for the following reaction?

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

Question 73

Provide the major organic product of the following reaction.

Question 74

Provide the major organic product of the reaction below.

Question 75

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

Question 76

Provide the major organic product of the reaction below.

Question 77

Provide the major organic product of the reaction below.

Question 78

Give the major product for the following reaction.

A)
B)
C)
D)
E)no reaction

Question 79

What is the major product from the following reaction?

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

Question 80

Give the major product for the following reaction.