Question 1

Which of the following is the IUPAC name of tert-butyl alcohol?

Accepted Answer

A)  1-butanol 
B)  2-butanol 
C)  2-methyl-1-propanol 
D)  2-methyl-2-propanol 
A)  1-butanol 
B)  2-butanol 
C)  2-methyl-1-propanol 
D)  2-methyl-2-propanol

Question 2

Which of the following is obtained from the oxidation of sec-butyl alcohol with potassium dichromate in aqueous sulfuric acid?

Accepted Answer

A)    
B)    
C)  both of these 
D)  neither of these 
A)    
B)    
C)  both of these 
D)  neither of these

Question 3

What is the smallest number of carbon atoms that can be found in an ether?

Accepted Answer

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

Question 4

What is the common name of the following compound?

Accepted Answer

A)  hexyl ether 
B)  propyl isopropyl ether 
C)  isopropyl propyl ether 
D)  dipropyl ether 
A)  hexyl ether 
B)  propyl isopropyl ether 
C)  isopropyl propyl ether 
D)  dipropyl ether

Question 5

Which of the following bonds is present in all ethers?

Accepted Answer

A)  C-S-H 
B)  O-C-F 
C)  C-O-C. 
D)  C-O-C 
A)  C-S-H 
B)  O-C-F 
C)  C-O-C. 
D)  C-O-C

Question 6

Which of the following statements is true of the products formed by heating the given compound with concentrated sulfuric acid?

Accepted Answer

A)  The major product is 2-methyl-2-hexene, and the minor product is 2-methyl-3-hexene. 
B)  The major product is 2-methyl-3-hexene, and the minor product is 2-methyl-2-hexene. 
C)  The only product formed is 2-methyl-1-hexene. 
D)  The only product formed is 2-methyl-3-hexene. 
A)  The major product is 2-methyl-2-hexene, and the minor product is 2-methyl-3-hexene. 
B)  The major product is 2-methyl-3-hexene, and the minor product is 2-methyl-2-hexene. 
C)  The only product formed is 2-methyl-1-hexene. 
D)  The only product formed is 2-methyl-3-hexene.

Question 7

What is the correct order of the boiling points of hexane, pentanol, and ethoxypropane?

Accepted Answer

A)  hexane > ethoxypropane > pentanol 
B)  hexane > pentanol > ethoxypropane 
C)  pentanol > ethoxypropane > hexane 
D)  pentanol > hexane > ethoxypropane 
A)  hexane > ethoxypropane > pentanol 
B)  hexane > pentanol > ethoxypropane 
C)  pentanol > ethoxypropane > hexane 
D)  pentanol > hexane > ethoxypropane

Question 8

Which of the following compounds is likely to have an unpleasant odor?

Accepted Answer

A)  CH3CH2OH 
B)  CH3CH2OCH2CH3 
C)  CH3CH2SH 
D)  HOCH2CH2OH 
A)  CH3CH2OH 
B)  CH3CH2OCH2CH3 
C)  CH3CH2SH 
D)  HOCH2CH2OH

Question 9

Which of the following is the IUPAC name of sec-butyl alcohol?

Accepted Answer

A)  1-butanol 
B)  2-butanol 
C)  2-methyl-1-propanol 
D)  2-methyl-2-propanol 
A)  1-butanol 
B)  2-butanol 
C)  2-methyl-1-propanol 
D)  2-methyl-2-propanol

Question 10

Which of the following statements is true of dimethyl ether and ethanol?

Accepted Answer

A)  The boiling points of dimethyl ether and ethanol are the same. 
B)  The boiling point of dimethyl ether is higher than the boiling point of ethanol. 
C)  The boiling point of dimethyl ether is lower than the boiling point of ethanol. 
D)  The boiling point of dimethyl ether is twice the boiling point of ethanol. 
A)  The boiling points of dimethyl ether and ethanol are the same. 
B)  The boiling point of dimethyl ether is higher than the boiling point of ethanol. 
C)  The boiling point of dimethyl ether is lower than the boiling point of ethanol. 
D)  The boiling point of dimethyl ether is twice the boiling point of ethanol.

Question 11

Which of the following reagents is used to convert ethylene to ethylene oxide?

Accepted Answer

A)  HCl in the presence of water 
B)  O2 in the presence of a catalyst 
C)  sulfuric acid in the presence of water 
D)  sulfuric acid in the presence of heat 
A)  HCl in the presence of water 
B)  O2 in the presence of a catalyst 
C)  sulfuric acid in the presence of water 
D)  sulfuric acid in the presence of heat

Question 12

Identify a statement that is true of the hydroxyl functional groups in 1,2,3-propanetriol.

Accepted Answer

A)  Two hydroxyl groups are bonded to two 1° carbons, and the third hydroxyl group is bonded to a 3° carbon. 
B)  Two hydroxyl groups are bonded to two 2° carbons, and the third hydroxyl group is bonded to a 3° carbon. 
C)  Two hydroxyl groups are bonded to two 3° carbons, and the third hydroxyl group is bonded to a 2° carbon. 
D)  Two hydroxyl groups are bonded to two 1° carbons, and the third hydroxyl group is bonded to a 2° carbon. 
A)  Two hydroxyl groups are bonded to two 1° carbons, and the third hydroxyl group is bonded to a 3° carbon. 
B)  Two hydroxyl groups are bonded to two 2° carbons, and the third hydroxyl group is bonded to a 3° carbon. 
C)  Two hydroxyl groups are bonded to two 3° carbons, and the third hydroxyl group is bonded to a 2° carbon. 
D)  Two hydroxyl groups are bonded to two 1° carbons, and the third hydroxyl group is bonded to a 2° carbon.

Question 13

Which of the following ethers was frequently used in the past as an anesthetic?

Accepted Answer

A)  diethyl ether 
B)  dimethyl ether 
C)  ethyl methyl ether 
D)  ethyl propyl ether 
A)  diethyl ether 
B)  dimethyl ether 
C)  ethyl methyl ether 
D)  ethyl propyl ether

Question 14

How many different alkene products (counting the cis and trans isomers of a compound as a single product) can be produced when 3-methyl-3-pentanol is dehydrated?

Accepted Answer

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

Question 15

What is the approximate pKa of a thiol?

Accepted Answer

A)  5 
B)  7 
C)  10 
D)  14 
A)  5 
B)  7 
C)  10 
D)  14

Question 16

Which of the following statements is true of oxidation reactions in primary or secondary alcohols?

Accepted Answer

A)  The alcohols lose oxygen atoms when oxidized. 
B)  The alcohols gain electrons when oxidized. 
C)  The alcohols lose hydrogen atoms when oxidized. 
D)  The alcohols lose water when oxidized. 
A)  The alcohols lose oxygen atoms when oxidized. 
B)  The alcohols gain electrons when oxidized. 
C)  The alcohols lose hydrogen atoms when oxidized. 
D)  The alcohols lose water when oxidized.

Question 17

Which of the following alcohols has the highest boiling point?

Accepted Answer

A)  1-pentanol 
B)  1,5-pentanediol 
C)  1,3,5-pentanetriol 
D)  1-butanol 
A)  1-pentanol 
B)  1,5-pentanediol 
C)  1,3,5-pentanetriol 
D)  1-butanol

Question 18

What is the approximate H-C-O bond angle in an alcohol?

Accepted Answer

A)  90° 
B)  109° 
C)  120° 
D)  180° 
A)  90° 
B)  109° 
C)  120° 
D)  180°

Question 19

What is the approximate C-O-C bond angle in noncyclic ethers?

Accepted Answer

A)  90° 
B)  109° 
C)  120° 
D)  180° 
A)  90° 
B)  109° 
C)  120° 
D)  180°

Question 20

How many different alkene products (counting the cis and trans isomers of a compound as a single product) can be formed when 2,3-dimethyl-3-pentanol is dehydrated?

Accepted Answer

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

Exam 13: Alcohols, Ethers, and Thiols

Which of the following is the IUPAC name of tert-butyl alcohol?

Which of the following is obtained from the oxidation of sec-butyl alcohol with potassium dichromate in aqueous sulfuric acid?

What is the smallest number of carbon atoms that can be found in an ether?

What is the common name of the following compound?

Which of the following bonds is present in all ethers?

Which of the following statements is true of the products formed by heating the given compound with concentrated sulfuric acid?

What is the correct order of the boiling points of hexane, pentanol, and ethoxypropane?

Which of the following compounds is likely to have an unpleasant odor?

Which of the following is the IUPAC name of sec-butyl alcohol?

Which of the following statements is true of dimethyl ether and ethanol?

Which of the following reagents is used to convert ethylene to ethylene oxide?

Identify a statement that is true of the hydroxyl functional groups in 1,2,3-propanetriol.

Which of the following ethers was frequently used in the past as an anesthetic?

How many different alkene products (counting the cis and trans isomers of a compound as a single product) can be produced when 3-methyl-3-pentanol is dehydrated?

What is the approximate pKa of a thiol?

Which of the following statements is true of oxidation reactions in primary or secondary alcohols?

Which of the following alcohols has the highest boiling point?

What is the approximate H-C-O bond angle in an alcohol?

What is the approximate C-O-C bond angle in noncyclic ethers?

How many different alkene products (counting the cis and trans isomers of a compound as a single product) can be formed when 2,3-dimethyl-3-pentanol is dehydrated?

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