Deck 16: Aldehydes and Ketones

Question 1

Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following product by addition of the Grignard reagent derived from the alkyl bromide to the carbonyl compound?

A) only 1 and 2
B) only 3 and 4
C) only 2 and 3
D) only 1, 2 and 3

Answer 1

only 1 and 2

Question 2

What is the major organic product obtained from the following reaction?

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

Answer 2

2

Question 3

Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following product by addition of the Grignard reagent derived from the alkyl bromide to the carbonyl compound?

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

Answer 3

only 2 and 3

Question 4

What is the major organic product obtained from the following reaction?

A) 2-phenyl-2-butanol
B) 3-phenyl-2-butanol
C) 3-phenylbutanone
D) propiophenone, PhCOCH₂CH₃

Question 5

What is the IUPAC name of the following compound?

A) (E)-4-methyl-4-hepten-3-one
B) (Z)-4-methyl-4-hepten-3-one
C) (E)-4-methyl-3-hepten-5-one
D) (Z)-4-methyl-3-hepten-5-one

Question 6

What is the correct assignment of the names of the following aldehydes and ketones?

A) 1 = acetone; 2 = acetaldehyde; 3 = formaldehyde
B) 1 = acetaldehyde; 2 = acetophenone; 3 = benzophenone
C) 1 = formaldehyde; 2 = acetaldehyde; 3 = acetone
D) 1 = acetaldehyde; 2 = acetone; 3 = acetophenone

Question 7

What is the IUPAC name of the following compound?

A) 4-phenyl-3-hexanone
B) 3-phenyl-4-hexanone
C) 1,2-diethyl-2-phenylethanal
D) 1-methyl-1-phenyl-2-butanone

Question 8

What is the IUPAC name of the following compound?

A) 3-methyl-3-phenylpropanol
B) 3-phenylbutanal
C) 3-phenyl-1-butanone
D) 3-phenylbutanoic acid

Question 9

What is the major organic product obtained from the following reaction?

A) 1-phenyl-1-butanol
B) 1-phenyl-2-butanol
C) 2-phenyl-1-butanol
D) butyrophenone, PhCOCH₂CH₂CH₃

Question 10

What is the major organic product obtained from the following sequence of reactions?

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

Question 11

What is the major organic product obtained from the following reaction?

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

Question 12

What is the correct assignment of the names of the following ketones?

A) 1 = acetone; 2 = phenol; 3 = benzaldehyde
B) 1 = acetone; 2 = acetophenone; 3 = benzophenone
C) 1 = formaldehyde; 2 = benzaldehyde; 3 = acetophenone
D) 1 = acetaldehyde; 2 = acetophenone; 3 = benzaldehyde

Question 13

What is the major organic product obtained from the following reaction?

A) 2,3-dimethyl-3-heptanol
B) 2,4-dimethyl-4-heptanol
C) 3,5-dimethyl-4-heptanol
D) 3,5-dimethyl-3-heptanol

Question 14

Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following product by addition of the Grignard reagent derived from the alkyl bromide to the carbonyl compound?

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

Question 15

What is the major organic product obtained from the following reaction?

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

Question 16

What is the IUPAC name of the following compound?

A) (2S,4R)-dimethylpentanal
B) (2S,4S)-dimethylpentanal
C) (R)-2,4-dimethylpentanal
D) (S)-2,4-dimethylpentanal

Question 17

What is the major organic product obtained from the following reaction?

A) 2,3-dimethyl-3-heptanol
B) 2,4-dimethyl-4-heptanol
C) 2,5-dimethyl-4-heptanol
D) 2,5-dimethyl-3-heptanol

Question 18

What is the IUPAC name of the following compound?

A) 4,4-diethyl-3-buten-2-one
B) 4-ethyl-3-hexen-2-one
C) (Z)-4-ethyl-3-hexen-2-one
D) 3-ethyl-4-hexen-5-one

Question 19

Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following product by addition of the Grignard reagent derived from the alkyl bromide to the carbonyl compound?

A) only 1 and 2
B) only 3 and 4
C) only 2 and 3
D) only 1, 2 and 3

Question 20

What is the IUPAC name of the following compound?

A) (S)-3,4,4-trimethylpentanal
B) (R)-3,4,4-trimethylpentanal
C) (R)-3-tert-butyl-3-methylpropanal
D) (R)-3-tert-butylbutanal

Question 21

What is the major organic product obtained from the following reaction?

A) (E)-3-methyl-2-pentene
B) (Z)-3-methyl-2-pentene
C) 2-methyl-2-pentene
D) 4-methyl-1-pentene

Question 22

Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following product by reaction of the Wittig reagent derived from the alkyl bromide with the carbonyl compound?

A) only 1 and 2
B) only 2 and 4
C) only 2 and 3
D) only 1, 2 and 3

Question 23

What is the major organic product obtained from the following reaction?

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

Question 24

Which ketone-diol undergoes cyclization to form the following acetal?

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

Question 25

What is the correct assignment of the names of the following functional groups?

A) 1 = imine; 2 = amine; 3 = hydrazone; 4 = oxime
B) 1 = hydrazone; 2 = amine; 3 = imine; 4 = oxime
C) 1 = oxime; 2 = imine; 3 = amine; 4 = hydrazone
D) 1 = imine; 2 = hydrazone; 3 = oxime; 4 = amine

Question 26

What is the major organic product obtained from the following reaction?

A) 1-butene
B) 2-butene
C) 2-methylpropene
D) 2-methyl-1-propanol

Question 27

What is the correct assignment of the names of the following functional groups?

A) 1 = enol; 2 = hydrate; 3 = acetal; 4 = hemiacetal
B) 1 = acetal; 2 = hydrate; 3 = enol; 4 = hemiacetal
C) 1 = hydrate; 2 = hemiacetal; 3 = acetal; 4 = enol
D) 1 = enol; 2 = hydrate; 3 = hemiacetal; 4 = enol

Question 28

What is the major organic product obtained from the following reaction?

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

Question 29

What is the major organic product obtained from the following reaction?

A) (E)-3-methyl-2-pentene
B) (Z)-3-methyl-2-pentene
C) 2-methyl-2-pentene
D) 4-methyl-1-pentene

Question 30

Which of the following is not true about the Wittig reaction?

A) triphenylphosphine reacts with 2° alkyl bromides by an S_N2 reaction to give an alkyltriphenylphosphonium bromide
B) alkyltriphenylphosphonium bromides are deprotonated by strong bases to give a phosphonium ylide
C) phosphonium ylids are nucleophilic
D) the product of the Wittig reaction is an alkyne

Question 31

What is the major organic product obtained from the following reaction?

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

Question 32

What is the correct assignment of the names of the following functional groups?

A) 1 = imine; 2 = amine; 3 = hydrazone; 4 = oxime
B) 1 = hydrazone; 2 = amine; 3 = imine; 4 = oxime
C) 1 = oxime; 2 = imine; 3 = amine; 4 = hydrazone
D) 1 = imine; 2 = hydrazone; 3 = oxime; 4 = amine

Question 33

What is the major organic product obtained from the following reaction?

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

Question 34

Which ketone-diol undergoes cyclization to form the following acetal?

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

Question 35

What is the major organic product obtained from the following reaction?

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

Question 36

What is the correct assignment of the names of the following functional groups?

A) 1 = acetal; 2 = hydrate; 3 = acetal; 4 = hemiacetal
B) 1 = acetal; 2 = enol; 3 = hydrate; 4 = hemiacetal
C) 1 = hydrate; 2 = hemiacetal; 3 = acetal; 4 = enol
D) 1 = enol; 2 = hydrate; 3 = hemiacetal; 4 = enol

Question 37

What is the major organic product obtained from the following reaction?

A) 2-methyl-2-heptene
B) 3-ethyl-2-pentene
C) (Z) 2-methyl-3-heptene
D) (E) 2-methyl-3-heptene

Question 38

What is the major organic product obtained from the following reaction?

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

Question 39

Which combination(s) of alkyl bromide and carbonyl compound can be used to prepare the following product by reaction of the Wittig reagent derived from the alkyl bromide with the carbonyl compound?

A) only 1 and 2
B) only 1 and 3
C) only 2 and 4
D) only 1, 2 and 3

Question 40

Which of the following is the best description of the overall transformation involved in a Wittig reaction?

A) addition
B) substitution
C) elimination
D) rearrangement

Question 41

What is the major organic product obtained from the following reaction?

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

Question 42

What is the major organic product obtained from the following reaction?

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

Question 43

What is the major organic product obtained from the following sequence of reactions?

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

Question 44

What is the major organic product obtained from the following reaction?

A) 2-pentanone
B) (E)-3-penten-2-ol
C) 2-pentanol
D) 4-hydroxy-2-pentanone

Question 45

What is the major organic product obtained from the following reaction?

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

Question 46

What is the major organic product obtained from the following reaction?

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

Question 47

What is the major organic product obtained from the following reaction?

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

Question 48

What is the major organic product obtained from the following sequence of reactions?

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

Question 49

What is the major organic product obtained from the following reaction?

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

Question 50

Which combination(s) of amine and carbonyl compound can be used to prepare the following product by reductive amination?

A) only 1 and 2
B) only 2 and 4
C) only 2 and 3
D) only 1, 2 and 3

Question 51

Which combination(s) of amine and carbonyl compound can be used to prepare the following product by reductive amination?

A) only 1
B) only 3
C) only 1 and 3
D) only 1, 2 and 4

Question 52

What is the major organic product obtained from the following reaction?

A) 2-pentanone
B) (E)-3-penten-2-ol
C) 2-pentanol
D) 4-hydroxy-2-pentanone

Question 53

What is the major organic product obtained from the following reaction?

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

Question 54

What is the major organic product obtained from the following reaction?

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

Question 55

What is the major organic product obtained from the following reaction?

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

Question 56

What is the major organic product obtained from the following reaction?

A) 2-methypentane
B) 4-methyl-2-pentanol
C) 4-methyl-1-pentene
D) (E) 4-methyl-2-pentene

Question 57

What is the major organic product obtained from the following reaction?

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

Question 58

What is the major organic product obtained from the following reaction?

A) 2-pentanol
B) pentane
C) 1-pentene
D) (E) 2-pentene

Question 59

What is the major organic product obtained from the following reaction?

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

Question 60

What is the major organic product obtained from the following reaction?

A) 2-pentanone
B) (E)-3-penten-2-ol
C) 2-pentanol
D) 4-hydroxy-2-pentanone

Question 61

Which of the following has the highest K_eq for enolization?

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

Question 62

An ¹H NMR is run on a sample. This spectrum is shown below. Based on this data the sample is probably an aldehyde.

Question 63

What is the major organic product obtained from the following sequence of reactions?

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

Question 64

What is the major organic product obtained from the following sequence of reactions?

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

Question 65

What is the reactivity of Br₂ in the acid-catalyzed bromination of acetophenone?

A) acid
B) base
C) nucleophile
D) electrophile

Question 66

Which of the following is the best description of the mechanism of the reaction between a ketone and an amine to form an imine?

A) concerted bimolecular substitution
B) nucleophilic addition followed by elimination
C) elimination followed by nucleophilic addition
D) electrophilic addition followed by rearrangement

Question 67

What is the relationship between the following two structures?

A) tautomers
B) constitutional isomers, but not tautomers
C) resonance structures
D) stereoisomers

Question 68

Of the types of reactions that characterize carbonyl groups, the following reaction would be classified as an α substitution.

Question 69

What type of reaction takes place upon treatment of a ketone with HCN to form a cyanohydrin?

A) nucleophilic addition
B) electrophilic addition
C) nucleophilic substitution
D) electrophilic substitution

Question 70

The correct name for the following compound is 3-oxoheptanal.

Question 71

What is the relationship between the following two structures?

A) tautomers
B) constitutional isomers, but not tautomers
C) resonance structures
D) stereoisomers

Question 72

What is the major organic product obtained from the following sequence of reactions?

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

Question 73

Which of the following statements is not true?

A) The reaction of a ketone with methanol in the presence of acid to give a acetal proceeds via a resonance stabilized cation
B) Protonation of a ketone increases its electrophilicity
C) The conversion of a hemiacetal to an acetal under acidic conditions proceeds via an S_N1 mechanism
D) The conversion of a hemiacetal to an acetal is catalyzed by both acid and base

Question 74

Which of the following is a reactive intermediate in the base-catalyzed racemization of (R)-3-phenyl-2-butanone?

A) carbanion
B) enol
C) enolate
D) radical

Question 75

What is the major organic product obtained from the following sequence of reactions?

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

Question 76

Which of the following statements is not true?

A) Reaction of benzophenone with methanol in the presence of acid gives a acetal
B) Reaction of butanal with ethanol in the presence of base gives an acetal
C) Reaction of benzaldehyde with ethanol in the presence of acid gives an acetal
D) Reaction of acetone with methanol in the presence of base gives a hemiacetal

Question 77

Which of the following is a reactive intermediate in the reaction of acetone with bromine in acetic acid to form 1-bromo-2-propanone?

A) carbanion
B) enol
C) enolate
D) radical

Question 78

Which of the following statements is not true?

A) The carbon atom of a carbonyl group is electrophilic
B) In general, aldehydes are more electrophilic than ketones
C) Nucleophilic addition to carbonyl groups can be catalyzed by acid or base
D) Addition of a nucleophile to a carbonyl group changes the hybridization of the carbonyl carbon from sp³ to sp² hybridization

Question 79

Which of the following has the highest K_eq for enolization?

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

Question 80

What is the relationship between the following two structures?

A) tautomers
B) constitutional isomers, but not tautomers
C) resonance structures
D) stereoisomers