Deck 17: Aldehydes and Ketones

Question 1

Which functional group is found in ketones?

A) −CHO
B) −CH₂OH
C) −COOH
D) RCOR'

Answer 1

D

Question 2

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

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

Answer 2

B

Question 3

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

Answer 3

C

Question 4

Which functional group is found in aldehydes?

A) −CHO
B) −CH₂OH
C) −COOH
D) RCOR'

Question 5

Which of the following is a correct IUPAC name?

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

Question 6

What is the IUPAC name for the following compound?

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

Question 7

What is the IUPAC name for the following compound?

A) 2,4-dimethyl-6-hexanal
B) 2-aldehydomethyl-4-methylpentane
C) 3,5-dimethyl-1-hexanal
D) 3,5-dimethylhexanal

Question 8

What is the IUPAC name of the following compound?

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

Question 9

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 10

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

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

Question 11

What is the IUPAC name of the following compound?

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

Question 12

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

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

Question 13

What is the IUPAC name for the following compound?

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

Question 14

Which of the following is true in naming aldehydes?

A) The root name is based on the longest carbon chain which contains the carbonyl carbon.
B) The oxygen atom is always bonded to C-1.
C) both a and b
D) neither a nor b

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

In the name 2-methyl-2-propenal the numbers represent which of the following?

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 alkene double bond
C) the position of the carbonyl group and the position of the alkene double bond
D) None of the above, since the name does not correspond to a real compound.

Question 17

Which of the following is true in naming ketones?

A) The root name is based on the longest carbon chain which contains the carbonyl carbon.
B) The oxygen atom is always bonded to C-1.
C) both a and b
D) neither a nor b

Question 18

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

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

Question 19

How many different aldehydes have the molecular formula C₄H₈O?

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

Question 20

What is the IUPAC name for the following compound?

A) 1-pentaldehyde
B) 1-pentanal
C) pentanal
D) pentanealdehyde

Question 21

Which of the following has the highest boiling point?

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

Question 22

What is the IUPAC name of the following compound?

A) (S)-2-hydroxycyclohexanone
B) (R)-2-hydroxycyclohexanone
C) (S)-1-hydroxy-2-cyclohexanone
D) (R)-1-hydroxy-2-cyclohexanone

Question 23

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

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

Question 24

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 25

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 26

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 27

How many different ketones have the molecular formula C₅H₁₀O?

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

Question 28

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 29

What is the IUPAC name for the following compound?

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

Question 30

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 31

What is the IUPAC name for the following compound?

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

Question 32

In which of the following can hydrogen bonding occur?

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

Question 33

How many different stereoisomers are possible for the following structure?

A) 1
B) 2
C) 4
D) 8

Question 34

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-dimethyl-1-hexanal

Question 35

In which of the following can hydrogen bonding occur?

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

Question 36

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

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

Question 37

In which of the following can hydrogen bonding occur?

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 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

Which of the following has the lowest boiling point?

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

Question 40

What is the IUPAC name of HOCH₂CH₂CHO ?

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

Question 41

Which of the following is most soluble in water?

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

Question 42

Which of the following statements is true?

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

Question 43

Which of the following has the lowest water solubility?

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

Question 44

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

A) carboxylic acids
B) ketones
C) both a and b
D) neither a nor b

Question 45

Which of the following has the highest boiling point?

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

Question 46

Which of the following has the highest boiling point?

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

Question 47

Which of the following is least soluble in water?

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

Question 48

Which of the following is most soluble in water?

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

Question 49

Which of the following is true of ketones?

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

Question 50

Which of the following has the lowest boiling point?

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

Question 51

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

A)
B)
C)
D) None of these products would be formed.

Question 52

Treatment of 2-hexanone with potassium dichromate in sulfuric acid will give which of the following products?

A) hexanal
B) hexanol
C) hexanoic acid
D) Unreacted 2-hexanone will be recovered.

Question 53

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 54

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

A) aldehydes
B) carboxylic acids
C) both a and b
D) neither a nor b

Question 55

Which of the following has the highest water solubility?

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

Question 56

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

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

Question 57

Which of the following has the lowest boiling point?

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

Question 58

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 59

Which of the following is obtained by oxidizing hexanal?

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

Question 60

Which of the following oxidizing agents oxidizes aldehydes in the body?

A) NADH
B) NAD⁺
C) O₂
D) none of these

Question 61

Which of the following is true of hemiacetals?

A) The most stable hemiacetals are noncyclic.
B) The most stable hemiacetals have four- or five-membered rings.
C) The most stable hemiacetals have five- or six-membered rings.
D) The most stable hemiacetals contain no OH groups.

Question 62

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

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

Question 63

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

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

Question 64

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

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

Question 65

In the reduction of an unsaturated aldehyde or ketone using H₂ in the presence of a transition metal catalyst, which of the following statements is true?

A) Both the C=C and C=O bonds are reduced at the same rate.
B) The C=C bond is reduced more rapidly than the C=O bond.
C) The C=O bond is reduced more rapidly than the C=C bond.
D) Unsaturated aldehydes and ketones do not undergo reduction under these conditions.

Question 66

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

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

Question 67

Which of these statements is true concerning the following reaction?

A) Both the C=C and C=O bonds will be reduced.
B) Only the C=C bond will be reduced.
C) Only the C=O bond will be reduced.
D) Neither the C=C nor C=O bond will be reduced.

Question 68

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

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 69

Which of the following will be obtained by the reduction of butanal using NaBH₄ followed by treatment with water?

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

Question 70

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

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

Question 71

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

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

Question 72

Which of the following is obtained by 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 73

Which type of biologically important molecules includes many cyclic hemiacetals?

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

Question 74

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

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

Question 75

Which of the following compounds contains an acetal functional group?

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

Question 76

Which of the following compounds contain a hemiacetal functional group?

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

Question 77

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

A)
B)
C)
D)

Question 78

Which of the following statements is true of hemiacetals?

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 79

Which of the following will be obtained by 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 80

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

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