Question 1

Ketones can be obtained by the oxidation of which of the following?

Accepted Answer

A)  1° alcohols 
B)  2° alcohols 
C)  3° alcohols 
D)  none of these 
A)  1° alcohols 
B)  2° alcohols 
C)  3° alcohols 
D)  none of these

Question 2

Which of the following classes of compounds react with sodium hydroxide to give a water-soluble salt?

Accepted Answer

A)  1° alcohols 
B)  phenols 
C)  both a and b 
D)  neither a nor b 
A)  1° alcohols 
B)  phenols 
C)  both a and b 
D)  neither a nor b

Question 3

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 a and b 
D)  neither a nor b 
A)    
B)    
C)  both a and b 
D)  neither a nor b

Question 4

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 5

Which of the following describes the products formed by the dehydration of trans-4-methylcyclohexanol?

Accepted Answer

A)  The only product is 4-methylcyclohexene. 
B)  The only product is 5-methylcyclohexene. 
C)  The major product is 4-methylcyclohexene and the minor product is 5-methylcyclohexene. 
D)  The major product is 5-methylcyclohexene and the minor product is 4-methylcyclohexene. 
A)  The only product is 4-methylcyclohexene. 
B)  The only product is 5-methylcyclohexene. 
C)  The major product is 4-methylcyclohexene and the minor product is 5-methylcyclohexene. 
D)  The major product is 5-methylcyclohexene and the minor product is 4-methylcyclohexene.

Question 6

Which of the following structures represents 4-methylcyclohexanol?

Accepted Answer

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

Question 7

Which of the following is the major source of glycerin used for industrial and commercial purposes?

Accepted Answer

A)  as a byproduct in the manufacture of soaps 
B)  a multi-step oxidation process from propene 
C)  the one step oxidation of methanol 
D)  none of the above 
A)  as a byproduct in the manufacture of soaps 
B)  a multi-step oxidation process from propene 
C)  the one step oxidation of methanol 
D)  none of the above

Question 8

If experimental conditions are carefully controlled, aldehydes can be obtained by the oxidation of which of the following?

Accepted Answer

A)  1° alcohols 
B)  2° alcohols 
C)  3° alcohols 
D)  all of these 
A)  1° alcohols 
B)  2° alcohols 
C)  3° alcohols 
D)  all of these

Question 9

Examine the structures represented by the following models. Atoms other than carbon and hydrogen are indicated by the element symbol.       A B C
-Which would have an acidic pKa?

Accepted Answer

A)  A 
B)  B 
C)  C 
D)  None of these are acidic. 
A)  A 
B)  B 
C)  C 
D)  None of these are acidic.

Question 10

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 11

Which of the following explains the fact that there is extensive hydrogen bonding in alcohols but little if any in thiols?

Accepted Answer

A)  Thiols are much more acidic than alcohols. 
B)  Sulfur is less electronegative than oxygen. 
C)  both a and b 
D)  neither a nor b 
A)  Thiols are much more acidic than alcohols. 
B)  Sulfur is less electronegative than oxygen. 
C)  both a and b 
D)  neither a nor b

Question 12

Which of the following statements are true? (i) 1-propanethiol has a higher boiling point than 1-propanol
(ii) 1-propanethiol has a comparable boiling point to CH3CH2SCH3 (ethyl methyl sulfide)
(iii) 1-propanethiol is much more acidic than 1-propanol.

Accepted Answer

A)  (i) and (ii) only 
B)  (i) and (iii) only 
C)  (ii) and (iii) only 
D)  (i), (ii) and (iii) 
A)  (i) and (ii) only 
B)  (i) and (iii) only 
C)  (ii) and (iii) only 
D)  (i), (ii) and (iii)

Question 13

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 14

Which of the following compounds has an extremely disagreeable odor?

Accepted Answer

A)  CH3CH2OH 
B)  CH3CH2OCH2CH3 
C)  CH3CH2SH 
D)  none of these 
A)  CH3CH2OH 
B)  CH3CH2OCH2CH3 
C)  CH3CH2SH 
D)  none of these

Question 15

How many different alkene products (counting cis and trans isomers of a compound as a single product) could 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 16

Which of the following describes the products formed by the dehydration of cis-2-methylcyclopentanol?

Accepted Answer

A)  The only product is 1-methylcyclopentene. 
B)  The only product is 3-methylcyclopentene. 
C)  The major product is 1-methylcyclopentene and the minor product is 3-methylcyclopentene. 
D)  The major product is 3-methylcyclopentene and the minor product is 1-methylcyclopentene. 
A)  The only product is 1-methylcyclopentene. 
B)  The only product is 3-methylcyclopentene. 
C)  The major product is 1-methylcyclopentene and the minor product is 3-methylcyclopentene. 
D)  The major product is 3-methylcyclopentene and the minor product is 1-methylcyclopentene.

Question 17

Which of the following statements are true? (i) the pKa of thiols is similar to that to phenols
(ii) little or no hydrogen bonding occurs between thiol molecules
(iii) thiols and disulfides are important in nucleic acid chemistry

Accepted Answer

A)  (i) and (ii) only 
B)  (i) and (iii) only 
C)  (ii) and (iii) only 
D)  (i), (ii) and (iii) 
A)  (i) and (ii) only 
B)  (i) and (iii) only 
C)  (ii) and (iii) only 
D)  (i), (ii) and (iii)

Question 18

What is the IUPAC name of tert-butyl mercaptan?

Accepted Answer

A)  2-butanethiol 
B)  2-methyl-1-propanethiol 
C)  2-methyl-2-propanethiol 
D)  none of these 
A)  2-butanethiol 
B)  2-methyl-1-propanethiol 
C)  2-methyl-2-propanethiol 
D)  none of these

Question 19

Negative side effects of the use of diethyl ether as an anesthetic include which of the following?

Accepted Answer

A)  greatly reduced blood pressure 
B)  highly increased pulse rate 
C)  irritation of the respiratory passages 
D)  all of these 
A)  greatly reduced blood pressure 
B)  highly increased pulse rate 
C)  irritation of the respiratory passages 
D)  all of these

Question 20

Which of the following is an important intermediate in the production of ethylene glycol?

Accepted Answer

A)  diethyl ether 
B)  ethanol 
C)  ethylene oxide 
D)  none of these 
A)  diethyl ether 
B)  ethanol 
C)  ethylene oxide 
D)  none of these

Exam 14: Alcohols, Ethers, and Thiols

Ketones can be obtained by the oxidation of which of the following?

Which of the following classes of compounds react with sodium hydroxide to give a water-soluble salt?

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

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

Which of the following describes the products formed by the dehydration of trans-4-methylcyclohexanol?

Which of the following structures represents 4-methylcyclohexanol?

Which of the following is the major source of glycerin used for industrial and commercial purposes?

If experimental conditions are carefully controlled, aldehydes can be obtained by the oxidation of which of the following?

Examine the structures represented by the following models. Atoms other than carbon and hydrogen are indicated by the element symbol. A B C -Which would have an acidic pKa?

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

Which of the following explains the fact that there is extensive hydrogen bonding in alcohols but little if any in thiols?

Which of the following statements are true? (i) 1-propanethiol has a higher boiling point than 1-propanol (ii) 1-propanethiol has a comparable boiling point to CH3CH2SCH3 (ethyl methyl sulfide) (iii) 1-propanethiol is much more acidic than 1-propanol.

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

Which of the following compounds has an extremely disagreeable odor?

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

Which of the following describes the products formed by the dehydration of cis-2-methylcyclopentanol?

Which of the following statements are true? (i) the pKa of thiols is similar to that to phenols (ii) little or no hydrogen bonding occurs between thiol molecules (iii) thiols and disulfides are important in nucleic acid chemistry

What is the IUPAC name of tert-butyl mercaptan?

Negative side effects of the use of diethyl ether as an anesthetic include which of the following?

Which of the following is an important intermediate in the production of ethylene glycol?

Matter, Energy, and Measurement

Atoms

Chemical Bonds

Chemical Reactions

Gases, Liquids, and Solids

Solutions and Colloids

Reaction Rates and Chemical Equilibrium

Acids and Bases

Nuclear Chemistry

Organic Chemistry

Alkanes

Alkenes and Alkynes

Benzene and Its Derivatives

Chirality: the Handedness of Molecules

Amines

Aldehydes and Ketones

Carboxylic Acids

Carboxylic Anhydrides, Esters, and Amides

Carbohydrates

Lipids

Proteins

Enzymes

Chemical Communications: Neurotransmitters and Hormones

Nucleotides, Nucleic Acids, and Heredity

Gene Expression and Protein Synthesis

Bioenergetics: How the Body Converts Food to Energy

Specific Catabolic Pathways: Carbohydrate, Lipid, and Protein Metabolism

Biosynthetic Pathways

Nutrition

Immunochemistry

Body Fluids

Filters

Examine the structures represented by the following models. Atoms other than carbon and hydrogen are indicated by the element symbol. A B C -Which would have an acidic pK_a?

Which of the following statements are true? (i) 1-propanethiol has a higher boiling point than 1-propanol (ii) 1-propanethiol has a comparable boiling point to CH₃CH₂SCH₃ (ethyl methyl sulfide) (iii) 1-propanethiol is much more acidic than 1-propanol.

Which of the following statements are true? (i) the pK_a of thiols is similar to that to phenols (ii) little or no hydrogen bonding occurs between thiol molecules (iii) thiols and disulfides are important in nucleic acid chemistry