Question 1

What is the approximate strength of a hydrogen bond in alcohols?

Accepted Answer

A)  less than 1 kcal/mol 
B)  2-5 kcal/mol 
C)  10-20 kcal/mol 
D)  more than 20 kcal/mol 
A)  less than 1 kcal/mol 
B)  2-5 kcal/mol 
C)  10-20 kcal/mol 
D)  more than 20 kcal/mol B

Question 2

When heated with concentrated sulfuric acid, which of the following alcohols will be converted to the following alkene as the major product?

Accepted Answer

A)    
B)    
C)  both   and
  
D)  none of these 
A)    
B)    
C)  both   and
  
D)  none of these C

Question 3

Identify a nonpolar covalent bond.

Accepted Answer

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

Question 4

Which of the following is obtained from the oxidation of isobutyl 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 5

When 1-pentanol, 2-pentanol, and 3-pentanol are dehydrated, which compound among them will yield only a single alkene product?

Accepted Answer

A)  only 1-pentanol 
B)  both 1-pentanol and 2-pentanol 
C)  both 1-pentanol and 3-pentanol 
D)  only 2-pentanol 
A)  only 1-pentanol 
B)  both 1-pentanol and 2-pentanol 
C)  both 1-pentanol and 3-pentanol 
D)  only 2-pentanol

Question 6

Which of the following is the IUPAC name of the following compound?

Accepted Answer

A)  isobutyl mercaptan 
B)  sec-butyl mercaptan 
C)  2-methyl-1-propanthiol 
D)  2-methyl-1-propanethiol 
A)  isobutyl mercaptan 
B)  sec-butyl mercaptan 
C)  2-methyl-1-propanthiol 
D)  2-methyl-1-propanethiol

Question 7

Which of the following is a tertiary alcohol?

Accepted Answer

A)  4-methyl-2-pentanol 
B)  trans-2-methylcyclohexanol 
C)  2-methyl-2-propanol 
D)  2,2-dimethyl-1-propanol 
A)  4-methyl-2-pentanol 
B)  trans-2-methylcyclohexanol 
C)  2-methyl-2-propanol 
D)  2,2-dimethyl-1-propanol

Question 8

Why do thiols show less hydrogen bonding than alcohols do?

Accepted Answer

A)  Thiols are much more acidic than alcohols. 
B)  The sulfur atoms in thiols are less electronegative than the oxygen atoms in alcohols. 
C)  Thiols are much more acidic than alcohols and the sulfur atoms in thiols are less electronegative than the oxygen atoms in alcohols. 
D)  None of these. 
A)  Thiols are much more acidic than alcohols. 
B)  The sulfur atoms in thiols are less electronegative than the oxygen atoms in alcohols. 
C)  Thiols are much more acidic than alcohols and the sulfur atoms in thiols are less electronegative than the oxygen atoms in alcohols. 
D)  None of these.

Question 9

Dehydration of which type of alcohol can never result in a mixture of products?

Accepted Answer

A)  1° 
B)  2° 
C)  3° 
D)  None, mixtures can be obtained from any of these. 
A)  1° 
B)  2° 
C)  3° 
D)  None, mixtures can be obtained from any of these.

Question 10

Which of the following is the IUPAC name of 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 11

Which of the following is a primary alcohol?

Accepted Answer

A)  2-methyl-2-propanol 
B)  4-methyl-2-pentanol 
C)  trans-2-methylcyclohexanol 
D)  2,2-dimethyl-1-propanol 
A)  2-methyl-2-propanol 
B)  4-methyl-2-pentanol 
C)  trans-2-methylcyclohexanol 
D)  2,2-dimethyl-1-propanol

Question 12

What is the correct order for the ease of dehydrating alcohols?

Accepted Answer

A)  tertiary > secondary > primary 
B)  tertiary > primary > secondary 
C)  primary > secondary > tertiary 
D)  secondary > tertiary > primary 
A)  tertiary > secondary > primary 
B)  tertiary > primary > secondary 
C)  primary > secondary > tertiary 
D)  secondary > tertiary > primary

Question 13

Which of the following alkenes will be the major product when 2-methylcyclohexanol is heated with concentrated sulfuric acid?

Accepted Answer

A)    
B)    
C)    
D)    
A)    
B)    
C)    
D)

Question 14

In addition to its use as an automobile antifreeze, how else is ethylene glycol used?

Accepted Answer

A)  as a component of various inks 
B)  as a solvent for paints 
C)  as a starting material in the manufacture of the polymer PET 
D)  all of these 
A)  as a component of various inks 
B)  as a solvent for paints 
C)  as a starting material in the manufacture of the polymer PET 
D)  all of these

Question 15

Which of the following reagents is used to convert menthol to menthone?

Accepted Answer

A)  phosphoric acid alone 
B)  sulfuric acid alone 
C)  sodium hydroxide in the presence of water 
D)  potassium dichromate in the presence of sulfuric acid 
A)  phosphoric acid alone 
B)  sulfuric acid alone 
C)  sodium hydroxide in the presence of water 
D)  potassium dichromate in the presence of sulfuric acid

Question 16

Why is the boiling point of ethanol greater than the boiling point of ethane?

Accepted Answer

A)  because ethanol is nonpolar, whereas ethane is polar 
B)  because unlike ethane, ethanol contains nonpolar covalent bonds 
C)  because unlike ethane, ethanol contains hydrogen bonds 
D)  because ethanol is aromatic, whereas ethane is aliphatic 
A)  because ethanol is nonpolar, whereas ethane is polar 
B)  because unlike ethane, ethanol contains nonpolar covalent bonds 
C)  because unlike ethane, ethanol contains hydrogen bonds 
D)  because ethanol is aromatic, whereas ethane is aliphatic

Question 17

Which of the following alcohols can be oxidized to ketones?

Accepted Answer

A)  1° alcohols 
B)  2° alcohols 
C)  both 1° and 2° alcohols 
D)  both 2° and 3° alcohols 
A)  1° alcohols 
B)  2° alcohols 
C)  both 1° and 2° alcohols 
D)  both 2° and 3° alcohols

Question 18

Which of the following is a characteristic of cyclic ethers?

Accepted Answer

A)  Cyclic ethers have a bond angle of 180° about the C-O-C bond. 
B)  They are compounds containing C-O-H bonds in which the oxygen involved in these bonds are part of the ring. 
C)  The oxygen atom of the C-O-C bond is part of the ring. 
D)  They are compounds containing C-O double bonds in which the carbon involved in this bond is part of the ring. 
A)  Cyclic ethers have a bond angle of 180° about the C-O-C bond. 
B)  They are compounds containing C-O-H bonds in which the oxygen involved in these bonds are part of the ring. 
C)  The oxygen atom of the C-O-C bond is part of the ring. 
D)  They are compounds containing C-O double bonds in which the carbon involved in this bond is part of the ring.

Question 19

Which of the following compounds is the most soluble in water?

Accepted Answer

A)  1-pentanol 
B)  propane 
C)  1-propanol 
D)  trans-2-butene 
A)  1-pentanol 
B)  propane 
C)  1-propanol 
D)  trans-2-butene

Question 20

Which of the following statements is true of the hydroxyl functional groups in 1,3-propanediol?

Accepted Answer

A)  One hydroxyl group is bonded to a 1° carbon, and the other hydroxyl group is bonded to a 2° carbon. 
B)  One hydroxyl group is bonded to a 1° carbon, and the other hydroxyl group is bonded to a 3° carbon. 
C)  Both the hydroxyl groups are bonded to a 1° carbon each. 
D)  Neither of the hydroxyl groups is bonded to a 1° carbon. 
A)  One hydroxyl group is bonded to a 1° carbon, and the other hydroxyl group is bonded to a 2° carbon. 
B)  One hydroxyl group is bonded to a 1° carbon, and the other hydroxyl group is bonded to a 3° carbon. 
C)  Both the hydroxyl groups are bonded to a 1° carbon each. 
D)  Neither of the hydroxyl groups is bonded to a 1° carbon.

Exam 13: Alcohols, Ethers, and Thiols

What is the approximate strength of a hydrogen bond in alcohols?

When heated with concentrated sulfuric acid, which of the following alcohols will be converted to the following alkene as the major product?

Identify a nonpolar covalent bond.

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

When 1-pentanol, 2-pentanol, and 3-pentanol are dehydrated, which compound among them will yield only a single alkene product?

Which of the following is the IUPAC name of the following compound?

Which of the following is a tertiary alcohol?

Why do thiols show less hydrogen bonding than alcohols do?

Dehydration of which type of alcohol can never result in a mixture of products?

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

Which of the following is a primary alcohol?

What is the correct order for the ease of dehydrating alcohols?

Which of the following alkenes will be the major product when 2-methylcyclohexanol is heated with concentrated sulfuric acid?

In addition to its use as an automobile antifreeze, how else is ethylene glycol used?

Which of the following reagents is used to convert menthol to menthone?

Why is the boiling point of ethanol greater than the boiling point of ethane?

Which of the following alcohols can be oxidized to ketones?

Which of the following is a characteristic of cyclic ethers?

Which of the following compounds is the most soluble in water?

Which of the following statements is true of the hydroxyl functional groups in 1,3-propanediol?

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