Deck 20: Aldehydes and Ketones

Question 1

Provide the structure for 2,3-dimethyl-2-octen-4-one.

Answer 1

Question 2

Provide the structure for m-nitroacetophenone.

Answer 2

Question 3

What is the correct structure for 3-methyl-5-(4-chlorophenyl)hexanal?

A) I
B) II
C) III
D) IV
E) V

Answer 3

II

Question 4

What is the IUPAC name for the following compound?

A) 5,5-dimethyl-2-heptanone
B) 5,5-dimethylcycloheptanone
C) 4,4-dimethylcycloheptanone
D) 3,3-dimethylcycloheptanone
E) none of these

Question 5

What is the structure for 5-hydroxy-2-phenyl-3-hexanone?

A) I
B) II
C) III
D) IV
E) V

Question 6

Provide the structure for 7-bromo-1-octyn-4-one.

A) I
B) II
C) III
D) IV
E) none of these

Question 7

What is the IUPAC name for the following compound?

Question 8

What is the IUPAC name for the following compound?

A) (S)-2-methyl-2-bromobutanone
B) (S)-2-bromo-2-methylcyclobutanone
C) (R)-2-bromo-2-methylcyclobutanone
D) (S)-1-bromo-1-methyl-2-cyclobutanone
E) (R)-1-bromo-1-methyl-2-cyclobutanone

Question 9

What is the IUPAC name for the following compound?

A) 4-benzylbutanal
B) 3-phenylpropanal
C) 3-benzylpropanal
D) 4-phenylbutanal
E) none of these

Question 10

What is the IUPAC name for the following compound?

A) 2-methyl-5-heptanone
B) 7-methyl-4-octanone
C) 6-isopropyl-4-octanone
D) isobutyl propyl ketone
E) 1,1-dimethyl-4-heptanone

Question 11

Provide the structure for 4-methylbenzaldehyde.

Question 12

What is the correct structure for 7-methyl-4-octanone?

A) I
B) II
C) III
D) IV
E) V

Question 13

What is the IUPAC name for the following compound?

Question 14

What is the IUPAC name for the following compound?

A) (R)-6-bromo-2-heptanal
B) (S)-6-bromo-2-heptanal
C) (R)-6-bromo-2-heptanone
D) (S)-6-bromo-2-heptanone
E) (R)-2-bromo-6-heptanone

Question 15

What is the IUPAC name for the following compound?

A) 2,5-dimethyl-6-hexanal
B) 2,5-dimethylhexanal
C) 1,4-dimethylpentanal
D) 1,4-dimethylhexanal
E) none of these

Question 16

What is the IUPAC name for the following compound?

A) 2,4-dimethyl-2-pentenone
B) 2,5-dimethylcyclopenten-3-one
C) 2,4-dimethylcyclopent-2-enone
D) 3,5-dimethylcyclopent-2-enone
E) 2-methyl-5-methylcyclopent-2-enone

Question 17

Provide the structure for (S)-3-chlorocyclohexanone.

Question 18

What is the IUPAC name for the following compound?

A) 4-oxo-5-phenyl-2-hexanol
B) 5-hydroxy-2-phenyl-3-hexanone
C) 2-hydroxy-5-phenyl-4-hexanone
D) 2-hydroxypropyl-1-phenylethyl ketone
E) 5-hydroxy-3-keto-2-phenylhexane

Question 19

What is the IUPAC name for the following compound?

A) 5-cyclohexyl-2-hexanal
B) 5-cyclohexyl-2-hexanone
C) 5-cyclohexyl-5-methyl-2-pentanone
D) 5-(1-methylcyclohexyl)-2-pentanone
E) 4-(1-methylcyclohexyl)-2-butanone

Question 20

What is the IUPAC name for the following compound?

Question 21

Predict the product for the following reaction.

A) hexanal
B) hexanoic acid
C) 2-hexanone
D) 2-chlorohexane
E) 1-hexanol

Question 22

Provide the reagents necessary to carry out the following conversion.

Question 23

Predict the product for the following reaction.

Question 24

Provide the reagents necessary to carry out the following conversion.

Question 25

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 26

Predict the major product for the following reaction

A) I
B) II
C) III
D) IV
E) none of these

Question 27

Predict the product for the following reaction.

A) cyclopentene
B) cyclopentanol
C) cyclopentanal
D) cyclopentanone
E) none of these

Question 28

What is the IUPAC name for the following compound?

Question 29

Predict the product for the following reaction.

Question 30

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 31

Compound A on ozonolysis yields the following two products What is the structure of compound A?

A) I
B) II
C) III
D) IV
E) none of these

Question 32

Compound A on ozonolysis yields 2,6-heptanedione. What is the structure of compound A?

A) 1,2-dimethylcyclohexene
1)
B) 2,6-dimethylcyclohexene
C) 1,5-dimethylcyclopentene
D)
1,2-dimethylcyclopentene
E)
2-methyl-1-cyclopentene

Question 33

Provide the reagents necessary to carry out the following conversion.

Question 34

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 35

Provide the structure for benzophenone.

Question 36

What is the IUPAC name for the following compound?

Question 37

Compound A on ozonolysis yields acetophenone and propanal. What is the structure of compound A?

A) 2-phenyl-2-pentene
B) 1-phenyl-1-hexene
C) 1-phenyl-2-pentene
D)
2-phenyl-2-hexene

Question 38

Predict the product for the following reaction.

A) 3-methyloctanone
B) 3-methyloctanal
C) 2-methyloctanone
D) 2-methyloctanal
E) 2-methyloctanoic acid

Question 39

What is the IUPAC name for the following compound?

Question 40

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 41

Predict the product for the following reaction

A) I
B) II
C) III
D) IV
E) V

Question 42

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 43

Which of the following statements is consistent with the mechanism for nucleophilic addition of aldehydes/ketones under basic conditions?

A) a proton transfer followed by a nucleophilic attack
B) a nucleophilic attack followed by a proton transfer
C) nucleophilic attack is the only step
D) proton transfer is not required

Question 44

Benzaldehyde is less reactive than ethanal towards nucleophilic addition reactions. Explain why using words as well as structural drawings.

Question 45

Provide the structure of the product, when cyclohexanecarbaldehyde reacts with excess 2-propanol in the presence of sulfuric acid.

A) I
B) II
C) III
D) IV
E) V

Question 46

Which of the following compounds is least reactive towards nucleophilic addition reaction?

A) I
B) II
C) III
D) IV
E) V

Question 47

A compound with an OH and OR group attached to the same carbon is known as ______.

A) an acetal
B) a hemiacetal
C) a hydrate
D) a vicinal hydrate
E) none of these

Question 48

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) none of these

Question 49

A compound with two OR groups attached to the same carbon is known as ______.

A) an acetal
B) a hemiacetal
C) a hydrate
D) a vicinal hydrate
E) none of these

Question 50

Which of the following reactions will produce acetophenone as a major product?

A) I
B) II
C) III
D) IV
E) all of these

Question 51

Provide the reagents necessary to carry out the following conversion.

Question 52

Predict the major product for the following reaction.

Question 53

Aldehydes are more reactive than ketones towards nucleophilic addition reactions. Explain why.

Question 54

Which of the following statements is consistent with the mechanism for nucleophilic addition of aldehydes/ketones under acidic conditions?

A) a proton transfer followed by a nucleophilic attack
B) a nucleophilic attack followed by a proton transfer
C) nucleophilic attack is the only step
D) proton transfer is not required

Question 55

Which of the following compounds is most reactive towards nucleophilic addition reaction?

A) I
B) II
C) III
D) IV
E) V

Question 56

Which of the following compounds can be classified as an acetal?

A) I
B) II
C) III
D) IV
E) none of these

Question 57

A compound with two OH groups attached to the same carbon is known as ______.

A) an acetal
B) a hemiacetal
C) a hydrate
D) a vicinal hydrate
E) none of these

Question 58

Which of the following compounds is least reactive towards nucleophilic addition reaction?

A) I
B) II
C) III
D) IV
E) Both I & IV

Question 59

Rank the following compounds in decreasing order (most to least) of reactivity towards nucleophilic addition reaction.

A) I>II>III>IV>V
B) II>IV>V>III>I
C) III>I>V>IV>II
D) I>III>II>IV>V
E) V>IV>II>III>I

Question 60

Which of the following compounds can be classified as a hemiacetal?

A) I
B) II
C) III
D) IV
E) none of these

Question 61

Predict the product when pentanal reacts with CH₃NH₂ in the presence of an acid catalyst.

A) I
B) II
C) III
D) IV
E) V

Question 62

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 63

Provide the reagents necessary to carry out the following conversion.

A) propanone / H₂SO₄
B) propanal/ H₂SO₄
C) 1-propanol/H₂SO₄
D) 2-propanol/ H₂SO₄
E) Ethanal/ H₂SO₄

Question 64

Predict the product for the following reaction sequence.

A) I
B) II
C) III
D) IV
E) V

Question 65

Provide the reagents necessary to carry out the following conversion.

Question 66

Predict the product(s) for the following reaction.

Question 67

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 68

Predict the product for the following reaction sequence.

Question 69

Which one of the following pairs of compounds will yield the following product in the presence of sulfuric acid?

A) I
B) II
C) III
D) IV
E) V

Question 70

Predict the product for the following reaction and provide a curved arrow mechanism for the formation of the product.

Question 71

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 72

Predict the product, when 4-methyl-2-hexanone reacts with hydrazine in the presence of an acid catalyst.

A) I
B) II
C) III
D) IV
E) V

Question 73

Predict the product for the following conversion.

Question 74

Provide the reagents necessary to carry out the following conversion.

Question 75

Provide the reagents necessary to carry out the following conversion.

Question 76

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 77

Predict the product for the following reaction and provide a curved arrow mechanism for the formation of the product.

Question 78

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) V

Question 79

Predict the product for the following reaction sequence.

A) I
B) II
C) III
D) IV
E) V

Question 80

Predict the product, when cyclopentanecarbaldehyde reacts with phenylhydrazine (PhNHNH₂) in the presence of an acid catalyst.

A) I
B) II
C) III
D) IV
E) V