Deck 16: Aldehydes and Ketones

Question 1

Which of the following is true of the IUPAC nomenclature of ketones?

A) The parent name is based on the longest carbon chain that contains the carbonyl carbon.
B) The oxygen atom is always bonded to the first carbon.
C) The parent name is based on the longest carbon chain that contains the carbonyl carbon, and the oxygen atom is always bonded to the first carbon.
D) None of these

Answer 1

A

Question 2

What is the IUPAC name of the following compound?

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

Answer 2

B

Question 3

What is the smallest number of carbon atoms that can be present in an aldehyde?

A) 1
B) 2
C) 3
D) 4

Answer 3

A

Question 4

If pairs of enantiomers are only counted once, how many different aldehydes have the molecular formula C₅H₁₀O?

A) 2
B) 3
C) 4
D) 5

Question 5

What is the IUPAC name of the following compound?

A) 2,4-dimethyl-6-heptanone
B) 4,6-dimethyl-2-heptanone
C) 4,6-dimethylheptanone
D) 2,4-dimethylhexanal

Question 6

What is the IUPAC name of the following compound?

A) 4-aldyltoluene
B) 4-toluylaldehyde
C) 1-methylbenzaldehyde
D) 4-methylbenzaldehyde

Question 7

What is the IUPAC name of the following compound?

A) 2,4-dimethyl-6-hexanal
B) 2-aldehydomethyl-4-methylpentane
C) 3,5-dimethyl-2-hexanal
D) 3,5-dimethylhexanal

Question 8

What is the IUPAC name of the following compound?

A) 1,1-dimethyl-3-pentanone
B) 3,3-methyl-1-pentanone
C) 3,3-dimethylcyclopentanone
D) 1,1-dimethyl-3-cyclopentanone

Question 9

Which structural feature is common to aldehydes and ketones?

A) an oxygen atom bonded to both a carbon atom and a hydrogen atom
B) an oxygen atom bonded to two carbon atoms
C) an oxygen atom double bonded to a carbon atom
D) two oxygen atoms bonded to the same carbon atom

Question 10

In the IUPAC name 2-methyl-2-propenal, what do the numbers represent?

A) the position of the methyl substituent and the position of the carbonyl group
B) the position of the methyl substituent and the position of the double bond
C) the position of the carbonyl group and the position of the double bond
D) the position of the carbonyl group and the position of the triple bond

Question 11

Which of the following is true of the IUPAC nomenclature of aldehydes?

A) The parent name is based on the longest carbon chain that contains the carbonyl carbon.
B) The oxygen atom is always bonded to the first carbon.
C) The parent name is based on the longest carbon chain that contains the carbonyl carbon and the oxygen atom is always bonded to the first carbon.
D) None of these

Question 12

Which of the following is a correct IUPAC name?

A) 1-methylpropanal
B) 2-methylpropanal
C) 3-methylpropanal
D) none of these

Question 13

Identify the IUPAC name of the given compound.

A) 1-propylbenzophenone
B) 1-phenyl-1-propanone
C) 1-propylphenylketone
D) 1-phenylpropyl ketone

Question 14

What is the IUPAC name of the following compound?

A) 1-pentaldehyde
B) pentanal
C) pentanoate
D) pentanone

Question 15

Which of the following is a correct IUPAC name?

A) 1-methylpropanal
B) 2-ethylpropanal
C) 2,2-dimethylpropanal
D) none of these

Question 16

What is the smallest number of carbon atoms that can be present in a ketone?

A) 1
B) 2
C) 3
D) 4

Question 17

Which functional group is found in ketones?

A) R-CHO
B) R-CH₂OH
C) R-COOH
D) R-COR'

Question 18

How many ketone functional groups are present in the following compound?

A) 2
B) 1
C) 4
D) 5

Question 19

How many different aldehydes have the molecular formula C₄H₈O?

A) 1
B) 2
C) 3
D) 4

Question 20

Which functional group is found in aldehydes?

A) R-CHO
B) R-CH₂OH
C) R-COOH
D) R-COR'

Question 21

What is the IUPAC name of propyl butyl ketone?

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

Question 22

What is the IUPAC name of propyl isobutyl ketone?

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

Question 23

How many different ketones have the molecular formula C₅H₁₀O?

A) 1
B) 2
C) 3
D) 4

Question 24

Which of the following compounds has the lowest boiling point?

A) butane
B) propanal
C) ethyl methyl ether
D) 1-propanol

Question 25

Which of the following compounds has the highest boiling point?

A) butane
B) propanal
C) ethyl methyl ether
D) 1-propanol

Question 26

Which of the following has intermolecular hydrogen bonds?

A) pure formaldehyde
B) pure acetone
C) a solution of formaldehyde in water
D) none of these

Question 27

What is the IUPAC name of the following compound?

A) 3-methyl-3-propylbutanal
B) 3-methyl-3-propyl-1-butanal
C) 3,3-dimethylhexanal
D) 3,3-methyl-1-hexanal

Question 28

What is the common name of 2-octanone?

A) methyl heptyl ketone
B) heptyl methyl ketone
C) methyl hexyl ketone
D) hexyl methyl ketone

Question 29

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

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

Question 30

What is the correct order of boiling points of the following compounds?

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

Question 31

What is the IUPAC name of HOCH₂CH₂CHO?

A) 1-hydroxy-3-propanal
B) 2-hydroxypropanal
C) 3-hydroxypropanal
D) 1,3-propanedial

Question 32

What is the correct order of boiling points of the following compounds?

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

Question 33

What is the IUPAC name of the following compound?

A) 1,1,1-trimethyl-2-propanone
B) 3,3-dimethyl-2-butanone
C) 3,3,3-trimethyl-2-propanone
D) 2,2-dimethyl-3-butanone

Question 34

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

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

Question 35

What is the IUPAC name of the following compound?

A) 2-methyl-3-amino-1-cyclopentanone
B) 3-amine-2-methyl-1-cyclopentanone
C) 2-methyl-3-aminocyclopentanone
D) 3-amino-2-methylcyclopentanone

Question 36

Which of the following has intermolecular hydrogen bonds?

A) pure acetone
B) pure formaldehyde
C) a mixture of acetone and formaldehyde
D) none of these

Question 37

Which of the following has intermolecular hydrogen bonds?

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

Question 38

What is the common name of 3-methyl-4-heptanone?

A) propyl butyl ketone
B) propyl sec-butyl ketone
C) propyl tert-butyl ketone
D) propyl isobutyl ketone

Question 39

What is the IUPAC name of the following compound?

A) 2,3-dihydroxycyclopentanone
B) 1,2-dihydroxy-3-cyclopentanone
C) cyclopentanone-1,2-diol
D) cyclopentanone-2,3-diol

Question 40

Identify the IUPAC name of the given compound.

A) 2-methyl-3-amino-1-cyclopentanone
B) 1-amino-2-methyl-3-cyclopentanone
C) 3-amino-2-methyl-1-cyclopentanone
D) 2-amino-1-methyl-2-cyclopentanone

Question 41

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

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

Question 42

Which of the following statements is true of aldehydes and ketones?

A) Both aldehydes and ketones are easily oxidized.
B) Neither aldehydes nor ketones are easily oxidized.
C) Aldehydes are easily oxidized, but ketones cannot be readily oxidized.
D) Ketones are easily oxidized, but aldehydes cannot be readily oxidized.

Question 43

Which of the following will give a positive test with Tollens' reagent?

A) aldehydes
B) ketones
C) aldehydes and ketones
D) none of these

Question 44

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

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

Question 45

Which of the following is true of liquid aldehydes?

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 46

Which product will be formed by the treatment of the following compound with silver nitrate and ammonia in water, followed by acidification with HCl?

A)
B)
C)
D) none of these

Question 47

Which of the following is an oxidizing agent?

A) NADH
B) H₂
C) O₂
D) none of these

Question 48

Which of the following compounds has the highest water solubility?

A) butanal
B) 1-butanol
C) 1-hexanol
D) hexanal

Question 49

Which of the following will generally give a positive test with Tollens' reagent?

A) carboxylic acids
B) ketones
C) both carboxylic acids and ketones
D) none of these

Question 50

Which of the following is true of ketones?

A) Most ketones are odorless.
B) Most ketones have mild, fishy odors.
C) Most ketones have strong, pleasant odors.
D) Most ketones have strong, unpleasant odors.

Question 51

Which of the following compounds has the lowest boiling point?

A) acetone
B) formaldehyde
C) 3-octanone
D) cyclopentanone

Question 52

Which of the following compounds is obtained by the oxidation of hexanal?

A) hexanol
B) 2-hexanone
C) hexanoic acid
D) none of these

Question 53

Which of the following compounds has the lowest water solubility?

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

Question 54

Which of the following compounds has the highest boiling point?

A) 2-butanone
B) 2-heptanone
C) 2-hexanone
D) 2-pentanone

Question 55

Which of the following will generally give a positive test with Tollens' reagent?

A) aldehydes
B) carboxylic acids
C) both aldehydes and carboxylic acids
D) none of these

Question 56

What is the final product obtained when 2-hexanone is treated with potassium dichromate in the presence of sulfuric acid?

A) an equilibrium mixture of 2-hexanone and hemiacetal
B) hexanol
C) hexanoic acid
D) none of these, as 2-hexanone does not undergo oxidation readily

Question 57

Which of the following compounds has the lowest boiling point?

A) 2-butanone
B) 2-heptanone
C) 2-hexanone
D) 2-pentanone

Question 58

Which of the following compounds has the highest boiling point?

A) acetone
B) butane
C) ethyl methyl ether
D) 2-propanol

Question 59

Which of the following is the least soluble in water?

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

Question 60

Which of the following compounds will undergo oxidation using potassium dichromate to form a carboxylic acid?

A) A and B only
B) A and C only
C) B only
D) C only

Question 61

Which of the following pairs of reactants produces a hemiacetal?

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

Question 62

Which of the following is obtained from the reaction of 2-butanone with H₂ in the presence of a transition metal catalyst?

A) 1-butene
B) 2-butene
C) 1-butanol
D) 2-butanol

Question 63

Which of the following compounds contain an acetal functional group?

A) A and B
B) A and C
C) B and C
D) only C

Question 64

What is produced by the reduction of pyruvate in the body under anaerobic conditions?

A) acetate
B) acetyl CoA
C) lactate
D) pyruvate

Question 65

Of the various -OH groups in the following carbohydrate, how many are part of the hemiacetal functional group?

A) 4
B) 1
C) 2
D) 3

Question 66

In biological systems, which of the following compounds reduces aldehydes and ketones?

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

Question 67

Which types of biologically important molecules include many cyclic hemiacetals?

A) carbohydrates
B) lipids
C) proteins
D) none of these

Question 68

Which of the following pairs of reactants produces a hemiacetal?

A) ketone and alcohol
B) ketone and aldehyde
C) ketone and carboxylic acid
D) none of these

Question 69

Which of the following compounds is obtained from the reaction of pentanal with H₂ in the presence of a transition metal catalyst?

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

Question 70

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

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

Question 71

What is the minimum number of oxygen atoms present in an acetal?

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

Question 72

Which of the following statements is correct regarding the reduction of an unsaturated aldehyde or ketone using H₂ in the presence of a transition metal catalyst?

A) Both the carbon-carbon and the carbon-oxygen double bonds are reduced at the same rate.
B) The carbon-carbon double bond is reduced more rapidly than the carbon-oxygen double bond.
C) The carbon-oxygen double bond is reduced more rapidly than the carbon-carbon double bond.
D) Unsaturated aldehydes and ketones do not undergo any reduction reactions under these conditions.

Question 73

Which of the following is true of hemiacetals?

A) The most stable hemiacetals are noncyclic.
B) Hemiacetals react with alcohols to form acetates.
C) Hemiacetals react with alcohols to form acetals.
D) Hemiacetals contain two carbonyl groups in their stable form.

Question 74

Which of the following compounds is obtained from the reduction of butanal using NaBH₄ followed by treatment with water?

A) butene
B) 1-butanol
C) 2-butanol
D) butanoic acid

Question 75

Which of the following compounds contain a hemiacetal functional group?

A) Α and B
B) Β and C
C) only B
D) only C

Question 76

Which of the following statements is true of hemiacetals?

A) All hemiacetals are generally stable.
B) All hemiacetals are unstable because of the presence of two carbonyl groups.
C) The functional group of hemiacetals is a carbon bonded to one -OH group and one -OR group.
D) Hemiacetals have two -OH groups bonded to the same carbon.

Question 77

Which of the following is the first step in the acid catalyzed formation of an acetal?

A) A proton is added to the carbonyl oxygen, giving a resonance-stabilized cation.
B) An electrophile and a nucleophile react to form a new covalent bond.
C) A proton is transferred from one oxygen to another oxygen.
D) A tertiary carbocation is formed by breaking the bond between a hydroxyl group and a carbon.

Question 78

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

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

Question 79

Which of following statements is correct regarding the following chemical reaction?

A) Both the carbon-carbon and the carbon-oxygen double bonds will be reduced.
B) Only the carbon-carbon double bond will be reduced.
C) Only the carbon-oxygen double bond will be reduced.
D) Neither the carbon-carbon double bond nor the carbon-oxygen double bond will be reduced.

Question 80

Which of the following compounds produces 1-pentanol upon reduction with an H₂/metal catalyst?

A)
B)
C)
D)