Question 1

Which of the following can undergo keto-enol tautomerism?

Accepted Answer

A)  2-methylpentanal 
B)  2,2-dimethylbutanal 
C)  both a and b 
D)  neither a nor b 
A)  2-methylpentanal 
B)  2,2-dimethylbutanal 
C)  both a and b 
D)  neither a nor b

Question 2

As a result of tautomerism, some hydroxyaldehydes can be converted to hydroxyketones, and vice versa. Which of the following compounds represents the intermediate formed when 2-hydroxybutanal is converted through tautomerism to 1-hydroxybutanone?

Accepted Answer

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

Question 3

Which of the following statements is true of hemiacetals?

Accepted Answer

A)  All hemiacetals are stable. 
B)  All hemiacetals are unstable. 
C)  Some cyclic hemiacetals are stable. 
D)  Hemiacetals have two OH groups bonded to the same carbon. 
A)  All hemiacetals are stable. 
B)  All hemiacetals are unstable. 
C)  Some cyclic hemiacetals are stable. 
D)  Hemiacetals have two OH groups bonded to the same carbon.

Question 4

In which of the following can hydrogen bonding occur?

Accepted Answer

A)  in a solution of acetone in water 
B)  in a solution of formaldehyde in water 
C)  in a solution of acetone and formaldehyde in water 
D)  in all of these cases 
A)  in a solution of acetone in water 
B)  in a solution of formaldehyde in water 
C)  in a solution of acetone and formaldehyde in water 
D)  in all of these cases

Question 5

Which of the following is most soluble in water?

Accepted Answer

A)  butanal 
B)  heptanal 
C)  hexanal 
D)  pentanal 
A)  butanal 
B)  heptanal 
C)  hexanal 
D)  pentanal

Question 6

What is the IUPAC name of propyl sec-butyl ketone?

Accepted Answer

A)  4-octanone 
B)  2-methyl-4-heptanone 
C)  3-methyl-4-heptanone 
D)  2,2-dimethyl-3-hexanone 
A)  4-octanone 
B)  2-methyl-4-heptanone 
C)  3-methyl-4-heptanone 
D)  2,2-dimethyl-3-hexanone

Question 7

Examine the following ball-and -stick model. Atoms other than carbon and hydrogen are labeled with the symbol of the element.   What would be the product of the reaction of this substance with AgNO3 in the presence of NH3?

Accepted Answer

A)  propanal 
B)  1-propanol 
C)  anion of propanoic acid 
D)  This substance does not react under these conditions. 
A)  propanal 
B)  1-propanol 
C)  anion of propanoic acid 
D)  This substance does not react under these conditions.

Question 8

Tautomers are examples of which of the following?

Accepted Answer

A)  constitutional isomers 
B)  diastereomers 
C)  enantiomers 
D)  none of these 
A)  constitutional isomers 
B)  diastereomers 
C)  enantiomers 
D)  none of these

Question 9

How many α−hydrogens are present in the following compound?

Accepted Answer

A)  0 
B)  1 
C)  2 
D)  3 
A)  0 
B)  1 
C)  2 
D)  3

Question 10

What is the IUPAC name for the following compound?

Accepted Answer

A)  4-hexanone 
B)  3-hexanone 
C)  ethyl propyl ketone 
D)  propyl ethyl ketone 
A)  4-hexanone 
B)  3-hexanone 
C)  ethyl propyl ketone 
D)  propyl ethyl ketone

Question 11

What is the IUPAC name of propyl isobutyl ketone?

Accepted Answer

A)  4-octanone 
B)  2-methyl-4-heptanone 
C)  3-methyl-4-heptanone 
D)  2,2-dimethyl-3-hexanone 
A)  4-octanone 
B)  2-methyl-4-heptanone 
C)  3-methyl-4-heptanone 
D)  2,2-dimethyl-3-hexanone

Question 12

What is the minimum number of oxygen atoms present in a hemiacetal?

Accepted Answer

A)  0 
B)  1 
C)  2 
D)  3 
A)  0 
B)  1 
C)  2 
D)  3

Question 13

Which of the following is true of liquid aldehydes?

Accepted Answer

A)  They are not readily oxidized. 
B)  They are not oxidized by O2 in the air, but are oxidized by stronger oxidizing agents. 
C)  They are readily oxidized by O2 in the air. 
D)  Their most important oxidation reaction is combustion. 
A)  They are not readily oxidized. 
B)  They are not oxidized by O2 in the air, but are oxidized by stronger oxidizing agents. 
C)  They are readily oxidized by O2 in the air. 
D)  Their most important oxidation reaction is combustion.

Question 14

Which of the following is obtained by the reaction of 2-pentanone with NaBH4 followed by addition of water?

Accepted Answer

A)  pentane 
B)  1-pentanol 
C)  2-pentanol 
D)  pentanoic acid 
A)  pentane 
B)  1-pentanol 
C)  2-pentanol 
D)  pentanoic acid

Question 15

In the formation of an acetal from an aldehyde, one mole of aldehyde requires which of the following as a coreactant?

Accepted Answer

A)  one mole of alcohol 
B)  two moles of alcohol 
C)  one mole of alcohol and one mole of water 
D)  two moles of water 
A)  one mole of alcohol 
B)  two moles of alcohol 
C)  one mole of alcohol and one mole of water 
D)  two moles of water

Question 16

Which of the following is least soluble in water?

Accepted Answer

A)  2-butanone 
B)  1-hydroxy-2-butanone 
C)  2,3-dihydroxybutanal 
D)  2-pentanone 
A)  2-butanone 
B)  1-hydroxy-2-butanone 
C)  2,3-dihydroxybutanal 
D)  2-pentanone

Question 17

Examine the following ball-and -stick model. Atoms other than carbon and hydrogen are labeled with the symbol of the element.   Which of the following is consistent with this structure?

Accepted Answer

A)  participates in hydrogen bonding with water 
B)  trigonal planar molecule 
C)  higher boiling point than the corresponding acid 
D)  all of the above 
A)  participates in hydrogen bonding with water 
B)  trigonal planar molecule 
C)  higher boiling point than the corresponding acid 
D)  all of the above

Question 18

In biological systems, aldehydes and ketones are reduced by which of the following?

Accepted Answer

A)  NADH2 
B)  NADH 
C)  NAD+ 
D)  none of these 
A)  NADH2 
B)  NADH 
C)  NAD+ 
D)  none of these

Question 19

Which of the following compounds is a tautomer of the following compound?

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

The reaction of which combination of reactants result in the formation of a hemiacetal?

Accepted Answer

A)  aldehyde and alcohol 
B)  aldehyde and amine 
C)  aldehyde and carboxylic acid 
D)  aldehyde and water 
A)  aldehyde and alcohol 
B)  aldehyde and amine 
C)  aldehyde and carboxylic acid 
D)  aldehyde and water

Exam 17: Aldehydes and Ketones

Which of the following can undergo keto-enol tautomerism?

As a result of tautomerism, some hydroxyaldehydes can be converted to hydroxyketones, and vice versa. Which of the following compounds represents the intermediate formed when 2-hydroxybutanal is converted through tautomerism to 1-hydroxybutanone?

Which of the following statements is true of hemiacetals?

In which of the following can hydrogen bonding occur?

Which of the following is most soluble in water?

What is the IUPAC name of propyl sec-butyl ketone?

Examine the following ball-and -stick model. Atoms other than carbon and hydrogen are labeled with the symbol of the element. What would be the product of the reaction of this substance with AgNO3 in the presence of NH3?

Tautomers are examples of which of the following?

How many α−hydrogens are present in the following compound?

What is the IUPAC name for the following compound?

What is the IUPAC name of propyl isobutyl ketone?

What is the minimum number of oxygen atoms present in a hemiacetal?

Which of the following is true of liquid aldehydes?

Which of the following is obtained by the reaction of 2-pentanone with NaBH4 followed by addition of water?

In the formation of an acetal from an aldehyde, one mole of aldehyde requires which of the following as a coreactant?

Which of the following is least soluble in water?

Examine the following ball-and -stick model. Atoms other than carbon and hydrogen are labeled with the symbol of the element. Which of the following is consistent with this structure?

In biological systems, aldehydes and ketones are reduced by which of the following?

Which of the following compounds is a tautomer of the following compound?

The reaction of which combination of reactants result in the formation of a hemiacetal?

Matter, Energy, and Measurement

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Chemical Bonds

Chemical Reactions

Gases, Liquids, and Solids

Solutions and Colloids

Reaction Rates and Chemical Equilibrium

Acids and Bases

Nuclear Chemistry

Organic Chemistry

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Benzene and Its Derivatives

Alcohols, Ethers, and Thiols

Chirality: the Handedness of Molecules

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Carboxylic Anhydrides, Esters, and Amides

Carbohydrates

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Bioenergetics: How the Body Converts Food to Energy

Specific Catabolic Pathways: Carbohydrate, Lipid, and Protein Metabolism

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Examine the following ball-and -stick model. Atoms other than carbon and hydrogen are labeled with the symbol of the element. What would be the product of the reaction of this substance with AgNO₃ in the presence of NH₃?

Which of the following is obtained by the reaction of 2-pentanone with NaBH₄ followed by addition of water?