Deck 8: Alcohols, Ethers, and Thiols

Question 1

4-(2-hydroxyethyl)-1-methylcyclohexanol reacts with HCl (gas) in diethyl ether at 5^oC. What is the main product formed?

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

Answer 1

II

Question 2

Arrange the compounds in the order of increasing acidity (least first).

A) III, I, II, IV
B) I, III, IV, II
C) II, III, I, IV
D) II, I, III, IV

Answer 2

II, III, I, IV

Question 3

2-(1-hydroxyprop-2-yl) cyclopentanol reacts with a mixture of potassium dichromate in concentrated sulfuric acid at room temperature. What product is formed?(Hint: assume that you have sufficient quantities of oxidizer to perform all possible reactions.)

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

Answer 3

IV

Question 4

Which are the best conditions for the preparation of 1-chloro-2-methylpropane starting from 2-methyl-1-propanol?

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

Question 5

Arrange the compounds in the order of increasing solubility in water (least soluble first). (help: estimate the hydrophobic surface of the non-polar part of the molecules)

A) II, III, I, IV
B) I, II, III, IV
C) IV, II, III, I
D) II, IV, III, I

Question 6

Arrange the compounds in the order of increasing solubility in water (least soluble first). (help: estimate the hydrophobic surface of the non-polar part of the molecules)

A) III, IV, II, I
B) II, III, IV, I
C) IV, III, II, I
D) III, IV, I, II

Question 7

4-(2-hydroxyethyl)-1-methylcyclohexanol reacts with HBr (gas) in dioxane under pressure at 125^oC. What is the main product formed?

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

Question 8

Which of the molecules are primary alcohols?

A) III, II
B) IV, I
C) II, III
D) I, II

Question 9

Which is the product of the following reaction?

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

Question 10

2-(1-hydroxyprop-2-yl) cyclopentanol reacts with pyridinium chlorochromate in dioxane under reflux. What product is formed?(Hint: assume that you have sufficient quantities of oxidizer to perform all possible reactions.)

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

Question 11

Which reagents do not perform the following conversion?

A) I, II
B) II, III
C) II, IV
D) I, III

Question 12

Which alcohol will form the most stable carbocation when treated with a strong mineral acid?

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

Question 13

Which is the product of the following reaction?

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

Question 14

Which is the major product of the following reaction?

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

Question 15

Arrange the compounds in the order of increasing solubility in water (least soluble first).

A) I, III, II, IV
B) III, I, IV, II
C) I, IV, II, III
D) IV, I, III, II

Question 16

Arrange the following in order of increasing rate of reactivity with HCl (least first).

A) I, II, IV, III
B) II, I, III, IV
C) IV, III, I, II
D) III, II, IV, I

Question 17

Which molecules are secondary alcohols?

A) I, III
B) II, III
C) III, IV
D) I, IV

Question 18

Which is the IUPAC name for the following structure?

A) cyclohexenol
B) 3-cyclohexen-1-ol
C) 1-cyclohexen-4-ol
D) 4-cyclohexenol

Question 19

The alcohol shown below reacts with thionyl chloride in pyridine. Which organic product is formed?

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

Question 20

Which is the best method for making the following conversion?

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

Question 21

Arrange the compounds in the order of increasing acidity (least acidic first).

A) II, III, IV, I
B) I, III, IV, II
C) III, IV, II, I
D) IV, II, III, I

Question 22

The major product of the following reaction is,

Question 23

Arrange the compounds in the order of increasing boiling point (lowest first).

A) II, I, III, IV
B) I, IV, II, III
C) IV, I, III, II
D) I, IV, III, II

Question 24

Arrange the compounds in the order of increasing acidity (least first).

A) II, I, III, IV
B) I, IV, II, III
C) III, II, I, IV
D) II, I, IV, III

Question 25

Classify the following reaction:

A) oxidation
B) reduction
C) neither
D) both

Question 26

The alkene shown below reacts with meta-chloroperbenzoic acid (MCPBA) in tetrahydrofuran. Which of the four formulas correctly describe the reaction products?

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

Question 27

The major product of the following reaction is,

Question 28

Which is the major product of the following reaction?

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

Question 29

Which is the major product from the acid catalyzed hydrolysis of cyclohexene oxide?

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

Question 30

The reagent needed to complete the following reaction is,

Question 31

The reagent needed to complete the following reaction is,

Question 32

Which is the major product of the following reaction?

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

Question 33

Classify the following transformation of a disulfide to two sulfides. How can that transformation be brought about?

A) oxidation
B) reduction
C) neither
D) both

Question 34

Which is the major product of the following reaction?

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

Question 35

Arrange the following in order of increasing ability to hydrogen bond (lowest first).

A) I, II, III, IV
B) III, I, IV, II
C) II, IV, I, III
D) I, IV, II, III

Question 36

The major product of the following reaction is,

Question 37

Arrange the compounds in the order of increasing acidity (least acidic first).

A) II, IV, I, III
B) III, IV, I, II
C) IV, III, II, I
D) I, III, IV, II

Question 38

Which is the major product of the following reaction?

A) 2-mercapto-2-methyl-3-pentanol
B) 3-mercapto-2-methyl-2-pentanol
C) 2-methyl-2,3-pentanediol
D) 4-methyl-3,4-pentanediol

Question 39

Which is the product of the following reaction?

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

Question 40

Which structures have the correct IUPAC name?

I: cis-1,2-dimethoxycyclohexane II: R-2-methoxy-1-propanol

III: 2-methoxypropane IV: trans-1,3-cyclohexanediol

A) I, II
B) III, IV
C) II, III
D) I, IV

Question 41

The strongest acid in the following list is water.

Question 42

The major product of the following reaction is,

Question 43

The following compounds are listed in decreasing boiling point order (highest first).

Question 44

The following compounds are listed in decreasing order of solubility in water (highest first).

Question 45

The following compound is named 1-chloro-2,2-dimethyl-4-pentanol.

Question 46

The major product of the reaction of 3-methyl-2-butanol with hot, concentrated sulfuric acid is 3-methyl-1-butene.

Question 47

The starting material needed to complete the following reaction is,

Question 48

The reaction arrows (curved arrows) required to complete the following reaction mechanisms are,

Question 49

The following compounds are listed in increasing order of solubility in water (lowest first).

Question 50

The starting material needed to complete the following reaction is,

Question 51

The reagent needed to complete the following reaction is,

Question 52

The major product of the reaction of 1-propanol with PCC is propanoic acid.

Question 53

The product of the reaction of methanol with sodium metal is sodium methoxide.

Question 54

The following compounds are listed in decreasing boiling point order (highest first).

Question 55

The following compound is named 2,6-dimethyl-1,4-cyclohexanediol.