Question 1

What is the smallest number of hydrogen atoms that can be found in a noncyclic ether?

Accepted Answer

A)  3 
B)  6 
C)  8 
D)  10 
A)  3 
B)  6 
C)  8 
D)  10

Question 2

Which of the following statements are true? (i) The pKa of thiols is similar to that of phenols.
(ii) Little or no hydrogen bonding occurs among 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) only 
A)  (i) and (ii) only 
B)  (i) and (iii) only 
C)  (ii) and (iii) only 
D)  (i), (ii), and (iii) only

Question 3

Which of the following processes is used to manufacture glycerin in bulk for industrial and commercial purposes?

Accepted Answer

A)  the hydrogenation of ethylene 
B)  the multistep oxidation process of propene 
C)  the one-step oxidation of methanol 
D)  none of these 
A)  the hydrogenation of ethylene 
B)  the multistep oxidation process of propene 
C)  the one-step oxidation of methanol 
D)  none of these

Question 4

Which of these compounds is obtained as the major product from the reaction of the following alkene with aqueous sulfuric acid?

Accepted Answer

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

Question 5

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

Accepted Answer

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

Question 6

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

Accepted Answer

A)  The only product formed is 1-methylcyclopentene. 
B)  The only product formed 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 formed is 1-methylcyclopentene. 
B)  The only product formed 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 7

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

Accepted Answer

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

Question 8

Which of the following products is formed by the oxidation of 2-hexanol with potassium dichromate?

Accepted Answer

A)  hexene 
B)  hexanal 
C)  cyclohexane 
D)  hexanone 
A)  hexene 
B)  hexanal 
C)  cyclohexane 
D)  hexanone

Question 9

Consider the following model. Elements other than hydrogen and carbon are labeled.   Which of the following is a characteristic of the given compound?

Accepted Answer

A)  It is soluble in water. 
B)  It has a pKa of about 10. 
C)  It readily reacts with NaOH to form a sodium salt. 
D)  All of these are characteristics of the compound. 
A)  It is soluble in water. 
B)  It has a pKa of about 10. 
C)  It readily reacts with NaOH to form a sodium salt. 
D)  All of these are characteristics of the compound.

Question 10

Which of the following statements are true? (i) 1-Propanethiol has a higher boiling point than 1-propanol.
(ii) 1-Propanethiol has a boiling point comparable 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 11

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 12

What is the IUPAC name of the following compound?

Accepted Answer

A)  2,2-dimethyl-4-butanol 
B)  3,3-dimethyl-1-butanol 
C)  1-tert-butyl-2-ethanol 
D)  2-sec-butyl-1-ethanol 
A)  2,2-dimethyl-4-butanol 
B)  3,3-dimethyl-1-butanol 
C)  1-tert-butyl-2-ethanol 
D)  2-sec-butyl-1-ethanol

Question 13

Which of the following statements is true of the hydroxyl functional groups in 2-methyl-1,2-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.

Question 14

Why are the boiling points of ethers similar to those of alkanes instead of alcohols?

Accepted Answer

A)  Both ether molecules and alkane molecules are polar, whereas alcohol molecules are nonpolar. 
B)  Hydrogen bonding between ether molecules is strong and this property is similar to that of alkanes. However, hydrogen bonding is weaker in alcohols than it is in both ethers and alkanes. 
C)  Although ether molecules are polar, they cannot form hydrogen bonds with other ether molecules. Similarly, alkane molecules do not form hydrogen bonds, whereas there is hydrogen bonding in alcohols. 
D)  None of these are correct explanations. 
A)  Both ether molecules and alkane molecules are polar, whereas alcohol molecules are nonpolar. 
B)  Hydrogen bonding between ether molecules is strong and this property is similar to that of alkanes. However, hydrogen bonding is weaker in alcohols than it is in both ethers and alkanes. 
C)  Although ether molecules are polar, they cannot form hydrogen bonds with other ether molecules. Similarly, alkane molecules do not form hydrogen bonds, whereas there is hydrogen bonding in alcohols. 
D)  None of these are correct explanations.

Question 15

Why are ethers more water soluble than alkanes of similar molecular weight and shape?

Accepted Answer

A)  because they are nonpolar compounds 
B)  because they can form hydrogen bonds with water 
C)  because they are similar to alkenes 
D)  because they have an oxygen bearing a partial positive charge 
A)  because they are nonpolar compounds 
B)  because they can form hydrogen bonds with water 
C)  because they are similar to alkenes 
D)  because they have an oxygen bearing a partial positive charge

Question 16

What is the major product obtained from the dehydration of 2,3-dimethyl-3-pentanol?

Accepted Answer

A)  2-isopropyl-2-butene 
B)  2,3-dimethyl-2-pentene 
C)  3,4-dimethyl-2-pentene 
D)  4,4-dimethyl-2-pentene 
A)  2-isopropyl-2-butene 
B)  2,3-dimethyl-2-pentene 
C)  3,4-dimethyl-2-pentene 
D)  4,4-dimethyl-2-pentene

Question 17

What is the IUPAC name of the following compound?

Accepted Answer

A)  2-methyl-4-hexanol 
B)  5-methyl-3-hexanol 
C)  3-hydroxy-5-methylhexane 
D)  4-hydroxy-2-methylhexane 
A)  2-methyl-4-hexanol 
B)  5-methyl-3-hexanol 
C)  3-hydroxy-5-methylhexane 
D)  4-hydroxy-2-methylhexane

Question 18

Which of the following statements is true of cis-3-isopropylcyclohexanol?

Accepted Answer

A)  Both the hydroxyl and the isopropyl groups lie in the plane that contains the cyclohexane ring. 
B)  Both the hydroxyl group and the isopropyl group lie above the plane that contains the cyclohexane ring. 
C)  The hydroxyl group lies above and the isopropyl group lies below the plane that contains the cyclohexane ring. 
D)  The hydroxyl group and the isopropyl group are bonded to the same carbon atom, and both groups lie in the same plane that contains the cyclohexane ring. 
A)  Both the hydroxyl and the isopropyl groups lie in the plane that contains the cyclohexane ring. 
B)  Both the hydroxyl group and the isopropyl group lie above the plane that contains the cyclohexane ring. 
C)  The hydroxyl group lies above and the isopropyl group lies below the plane that contains the cyclohexane ring. 
D)  The hydroxyl group and the isopropyl group are bonded to the same carbon atom, and both groups lie in the same plane that contains the cyclohexane ring.

Question 19

What is the product formed by the reaction of methanol with CO in the presence of a rhodium catalyst?

Accepted Answer

A)  formaldehyde 
B)  ethylene oxide 
C)  acetic acid 
D)  ethylene glycol 
A)  formaldehyde 
B)  ethylene oxide 
C)  acetic acid 
D)  ethylene glycol

Question 20

Identify a polar covalent bond in 3-buten-1-ol.

Accepted Answer

A)  carbon-carbon single bond 
B)  carbon-carbon single bond. 
C)  oxygen-hydrogen bond. 
D)  carbon-hydrogen bond 
A)  carbon-carbon single bond 
B)  carbon-carbon single bond. 
C)  oxygen-hydrogen bond. 
D)  carbon-hydrogen bond

Exam 13: Alcohols, Ethers, and Thiols

What is the smallest number of hydrogen atoms that can be found in a noncyclic ether?

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

Which of the following processes is used to manufacture glycerin in bulk for industrial and commercial purposes?

Which of these compounds is obtained as the major product from the reaction of the following alkene with aqueous sulfuric acid?

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

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

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

Which of the following products is formed by the oxidation of 2-hexanol with potassium dichromate?

Consider the following model. Elements other than hydrogen and carbon are labeled. Which of the following is a characteristic of the given compound?

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

What is the IUPAC name of the following compound?

What is the IUPAC name of the following compound?

Which of the following statements is true of the hydroxyl functional groups in 2-methyl-1,2-propanediol?

Why are the boiling points of ethers similar to those of alkanes instead of alcohols?

Why are ethers more water soluble than alkanes of similar molecular weight and shape?

What is the major product obtained from the dehydration of 2,3-dimethyl-3-pentanol?

What is the IUPAC name of the following compound?

Which of the following statements is true of cis-3-isopropylcyclohexanol?

What is the product formed by the reaction of methanol with CO in the presence of a rhodium catalyst?

Identify a polar covalent bond in 3-buten-1-ol.

Matter, Energy, and Measurement

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Alkenes, Alkynes, and Aromatic Compounds

Chirality: the Handedness of Molecules

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Filters

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

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