Question 1

In which class of compounds is the carbon at the functional group least highly oxidized?

Accepted Answer

A)  alcohols 
B)  aldehydes 
C)  carboxylic acids 
D)  ketones 
A)  alcohols 
B)  aldehydes 
C)  carboxylic acids 
D)  ketones

Question 2

Which of the following is true of liquid ethers?

Accepted Answer

A)  They are both volatile and highly flammable. 
B)  They are neither volatile nor highly flammable. 
C)  They are volatile, but are not flammable. 
D)  They are flammable, but are not volatile. 
A)  They are both volatile and highly flammable. 
B)  They are neither volatile nor highly flammable. 
C)  They are volatile, but are not flammable. 
D)  They are flammable, but are not volatile.

Question 3

Examine the structures represented by the following models. Atoms other than carbon and hydrogen are indicated by the element symbol.       A B C
-Which is most likely to be the least reactive?

Accepted Answer

A)  A 
B)  B 
C)  C 
D)  All are of equal reactivity. 
A)  A 
B)  B 
C)  C 
D)  All are of equal reactivity.

Question 4

What is the IUPAC name of sec-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 5

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 6

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 7

Which definition of oxidation is most useful when considering the oxidation of primary or secondary alcohols?

Accepted Answer

A)  gain of oxygen 
B)  loss of electrons 
C)  loss of hydrogen 
D)  None of these, 1° and 2° alcohols are not oxidized. 
A)  gain of oxygen 
B)  loss of electrons 
C)  loss of hydrogen 
D)  None of these, 1° and 2° alcohols are not oxidized.

Question 8

Which of the following alcohols is used as an oxygenate additive in gasoline used by conventional road vehicles?

Accepted Answer

A)  ethanol 
B)  isopropanol 
C)  methanol 
D)  none of these 
A)  ethanol 
B)  isopropanol 
C)  methanol 
D)  none of these

Question 9

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

Question 10

Which of the following reagents was used in the original breath alcohol test used by law enforcement officials?

Accepted Answer

A)  Cr3+ 
B)  hydrogen peroxide 
C)  potassium dichromate 
D)  none of these 
A)  Cr3+ 
B)  hydrogen peroxide 
C)  potassium dichromate 
D)  none of these

Question 11

Which of these responses describes the products formed by heating the following 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 major product is 2-methyl-2-hexene and the minor product is 2-methyl-1-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 major product is 2-methyl-2-hexene and the minor product is 2-methyl-1-hexene.

Question 12

What is the approximate C−O−C bond angle in the cyclic ether ethylene oxide, C2H4O?

Accepted Answer

A)  60° 
B)  90° 
C)  109° 
D)  120° 
A)  60° 
B)  90° 
C)  109° 
D)  120°

Question 13

What is the common name for the following compound?

Accepted Answer

A)  hexyl ether 
B)  propyl isopropyl ether 
C)  isopropyl propyl ether 
D)  none of these 
A)  hexyl ether 
B)  propyl isopropyl ether 
C)  isopropyl propyl ether 
D)  none of these

Question 14

Which of the following correctly gives the order of boiling points for the molecules propane, dimethyl ether, and ethanol?

Accepted Answer

A)  ethanol > dimethyl ether > propane 
B)  ethanol > propane > dimethyl ether 
C)  propane > dimethyl ether > ethanol 
D)  propane > ethanol > dimethyl ether 
A)  ethanol > dimethyl ether > propane 
B)  ethanol > propane > dimethyl ether 
C)  propane > dimethyl ether > ethanol 
D)  propane > ethanol > dimethyl ether

Question 15

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 the above 
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 the above

Question 16

Which of the following alcohols will undergo acid-catalyzed dehydration most easily?

Accepted Answer

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

Question 17

Oxidation of ethers with potassium dichromate gives which of the following types of product?

Accepted Answer

A)  aldehydes 
B)  carboxylic acids 
C)  ketones 
D)  None of these; ethers do not react with sodium dichromate. 
A)  aldehydes 
B)  carboxylic acids 
C)  ketones 
D)  None of these; ethers do not react with sodium dichromate.

Question 18

What is the IUPAC name of the following compound?

Accepted Answer

A)  2-ethyl-4-pentanol 
B)  4-methyl-2-hexanol 
C)  4-ethyl-2-pentanol 
D)  3-methyl-5-hexanol 
A)  2-ethyl-4-pentanol 
B)  4-methyl-2-hexanol 
C)  4-ethyl-2-pentanol 
D)  3-methyl-5-hexanol

Question 19

Which of the following is obtainable by the oxidation of tert-butyl alcohol?

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 20

Which of the alcohols shown below will react when heated with concentrated sulfuric acid to give the following alkene as the major product?

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

Exam 14: Alcohols, Ethers, and Thiols

In which class of compounds is the carbon at the functional group least highly oxidized?

Which of the following is true of liquid ethers?

Examine the structures represented by the following models. Atoms other than carbon and hydrogen are indicated by the element symbol. A B C -Which is most likely to be the least reactive?

What is the IUPAC name of sec-butyl mercaptan?

What is the approximate pKa of a thiol?

Which of the following alcohols has the highest boiling point?

Which definition of oxidation is most useful when considering the oxidation of primary or secondary alcohols?

Which of the following alcohols is used as an oxygenate additive in gasoline used by conventional road vehicles?

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

Which of the following reagents was used in the original breath alcohol test used by law enforcement officials?

Which of these responses describes the products formed by heating the following compound with concentrated sulfuric acid?

What is the approximate C−O−C bond angle in the cyclic ether ethylene oxide, C2H4O?

What is the common name for the following compound?

Which of the following correctly gives the order of boiling points for the molecules propane, dimethyl ether, and ethanol?

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

Which of the following alcohols will undergo acid-catalyzed dehydration most easily?

Oxidation of ethers with potassium dichromate gives which of the following types of product?

What is the IUPAC name of the following compound?

Which of the following is obtainable by the oxidation of tert-butyl alcohol?

Which of the alcohols shown below will react when heated with concentrated sulfuric acid to give the following alkene as the major product?

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

What is the approximate pK_a of a thiol?

What is the approximate C−O−C bond angle in the cyclic ether ethylene oxide, C₂H₄O?