Deck 19: Aldehydes and Ketones

Question 1

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

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

Answer 1

II

Question 2

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

Answer 2

(S)-2-bromo-2-methylcyclobutanone

Question 3

What is the correct structure for 5-methyl-4-octanone?

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

Answer 3

II

Question 4

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

A) I
B) II
C) III
D) IV
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 m-nitroacetophenone.

Question 7

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 8

What is the IUPAC name for the following compound?

Question 9

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

Question 10

Name the aldehyde or ketone that is found in nail polish remover.

A) ethanol
B) 2-butanone
C) acetone
D) formaldehyde
E) diethyl ether

Question 11

Name the aldehyde or ketone that is used as a preservative.

A) ethanol
B) 2-butanone
C) acetone
D) formaldehyde
E) diethyl ether

Question 12

Provide the structure for 4-methylbenzaldehyde.

Question 13

What is the IUPAC name for the following compound?

Question 14

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 15

What is the IUPAC name for the following compound?

Question 16

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 17

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 18

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) 1,1-dimethyl-4-cycloheptanone

Question 19

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

Question 20

What is the IUPAC name for the following compound?

A) 4-benzylbutanal
B) 3-phenylpropanal
C) 3-benzylpropanal
D) 4-phenylbutanal
E) 2-benzylethanal

Question 21

Provide the structure for benzophenone.

Question 22

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 23

Predict the product for the following reaction.

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

Question 24

Predict the product for the following reaction.

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

Question 25

Predict the product for the following reaction.

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

Question 26

Predict the product for the following reaction.

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

Question 27

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 28

Predict the product for the following reaction.

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

Question 29

What is the IUPAC name for the following compound?

Question 30

Predict the product for the following reaction.

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

Question 31

Predict the product for the following reaction.

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

Question 32

What is the IUPAC name for the following compound?

Question 33

Predict the product for the following reaction.

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

Question 34

Predict the product for the following reaction.

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

Question 35

Predict the product for the following reaction.

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

Question 36

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 37

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

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

Question 38

Predict the product for the following reaction.

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

Question 39

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 40

What is the IUPAC name for the following compound?

Question 41

Provide the reagents necessary to carry out the following conversion.

A) 1. H₂O/ H₂SO₄,
2) PCC/CH₂Cl₂
B) PCC/ CH₂Cl₂
C) 1. 9-BBN,
2) H₂O₂/NaOH/H₂O
D) 1. O₃,
2) Zn/acetic acid
E) 1. 9-BBN
2) H₂O₂/NaOH/H₂O
3) CrO₃/H₂SO₄/H₂O

Question 42

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

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

Question 43

Provide the reagents necessary to carry out the following conversion.

Question 44

Predict the product for the following reaction.

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

Question 45

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 46

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

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

Question 47

Predict the product for the following reaction.

Question 48

Predict the product for the following reaction.

Question 49

Provide the reagents necessary to carry out the following conversion.

Question 50

Predict the major product for the following reaction.

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

Question 51

Predict the product for the following reaction.

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

Question 52

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

Question 53

Predict the product for the following reaction.

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

Question 54

Provide the reagents necessary to carry out the following conversion.

Question 55

Provide the reagents necessary to carry out the following conversion.

Question 56

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

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

Question 57

Rank the following compounds in decreasing order (most to least) of reactivity towards a 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 58

Predict the major product for the following reaction.

Question 59

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

Question 60

Predict the product for the following reaction.

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

Question 61

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 62

Provide the reagents necessary to carry out the following conversion.

Question 63

Provide the reagents necessary to carry out the following conversion.

Question 64

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 65

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 66

Predict the product for the following conversion.

Question 67

Predict the product for the following reaction.

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

Question 68

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

Question 69

A compound with an OH and an 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 70

Predict the product for the following reaction.

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

Question 71

Predict the product for the following reaction.

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

Question 72

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

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

Question 73

Predict the product(s) for the following reaction.

Question 74

Predict the product for the following reaction.

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

Question 75

Predict the product for the following reaction.

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

Question 76

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 77

Predict the product for the following reaction.

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

Question 78

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

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

Question 79

Which of the following statements is consistent with the mechanism for the 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 80

Which of the following statements is consistent with the mechanism for the 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