Deck 10: Reactions of Alcohols, ethers, epoxides, amines and Sulfur-Containing Compounds

Question 1

Give the major organic product for the following reaction.

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

Answer 1

Question 2

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

Answer 2

Question 3

Give the major organic product for the following reaction.

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

Answer 3

Question 4

What is the major product of the following reaction?

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

Question 5

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 6

Why are alcohols typically poor electrophiles?

Question 7

What is the major product of the following reaction?

A)
B)
C)
D)
E)

Question 8

Give the major organic product for the following reaction.

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

Question 9

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

Question 10

Provide the major organic product of the reaction below.

Question 11

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

Question 12

Provide the major organic product of the reaction below.

Question 13

Provide the major organic product of the reaction below.

Question 14

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.

Question 15

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 16

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 17

Provide the major organic product of the reaction below.

Question 18

Provide the major organic product of the reaction below.

Question 19

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 20

Propose a mechanism for the following reaction.

Question 21

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 22

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

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

Provide the major organic product of the reaction below.

Question 26

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

Question 27

Give the major organic product for the following reaction.

A)
B)
C)
D)
E)

Question 28

What is the product of the following reaction?

A)
B)
C)
D)
E)

Question 29

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

Question 30

What is the major product of the following reaction?

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

Question 31

Provide the major organic product of the reaction below.

Question 32

Provide the major organic product of the reaction below.

Question 33

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

Question 34

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

Question 35

Provide the structure of the major organic product in the reaction below.
PhCH₂CH₂OH

Question 36

What is the product of the following reaction?

A)
B)
C)
D)
E)

Question 37

Give the major product for the following reaction.

Question 38

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

Question 39

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 40

Provide the major organic product of the reaction below.

Question 41

Provide the major organic product of the reaction below.

Question 42

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

Question 43

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

Question 44

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 45

Which of the following alcohols dehydrates with the fastest rate?

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

Question 46

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

Question 47

Give the major product for the following reaction.

A)
B)
C)
D)
E)

Question 48

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

Question 49

Give the major product for the following reaction.

A)
B)
C)
D)
E)

Question 50

Give the major product for the following reaction.

A)
B)
C)
D)
E)

Question 51

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

Question 52

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

Question 53

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

Question 54

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

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

Question 55

What is the product of the following reaction?

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

Question 56

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

Question 57

What is the major product of the following reaction?

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

Question 58

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

Question 59

Provide the major organic product of the reaction below.

Question 60

Provide the major organic product of the reaction below.

Question 61

Provide the major organic product of the reaction below.

Question 62

What is the major product for the following reaction?

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

Question 63

What is the major product for the following reaction?

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

Question 64

Give the major product for the following reaction.

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

Question 65

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

Question 66

Provide the major organic product of the reaction below.

Question 67

Provide the major organic product in the reaction below.

Question 68

What are the major products from the following reaction?

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

Question 69

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 70

Give the major organic product for the following reaction.

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

Question 71

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

Question 72

Provide the major organic product of the reaction below.

Question 73

Give the major product for the following reaction.

Question 74

Propose a mechanism for the following reaction:

Question 75

What is the major product from the following reaction?

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

Question 76

Provide the major organic product in the reaction below.

Question 77

What is the product from the following reaction?

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

Question 78

Give the major product for the following reaction.

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

Question 79

Provide the major organic product of the reaction below.

Question 80

Provide the major organic product of the following reaction.