Deck 16: Aldehydes and Ketones I Nucleophilic Addition to the Carbonyl Group

Question 1

What is the correct structure for 3-methyl-5-(2,5-dinitrophenyl)pentanal?

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

Answer 1

II

Question 2

What is the correct IUPAC name for the following compound?

A) (S)-3-chloro-1-hexanone
B) (S)-1-chloro-3-hexanone
C) (R)-3-chlorocyclohexanone
D) (S)-3-chlorocyclohexanone
E) (S)-1-chloro-3-cyclohexanone

Answer 2

(S)-3-chlorocyclohexanone

Question 3

What is the correct structure for 5,5-dimethyl-2-heptanone?

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

Answer 3

II

Question 4

What is the correct IUPAC name for the following compound?

A) 5,5-Dimethyl-2-heptanone
B) 5-Ethyl-5,5-dimethyl-Methyl-2-octanone
C) 5-Ethyl-5-methyl- 2-hexanone
D) 5,5-Dimethyl-2-octanone
E) 3,3-Dimethyl-6-heptanone

Question 5

What is the correct structure for 4-chloro-3-methylbenzaldehyde?

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

Question 6

What is the correct 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 7

What is the correct IUPAC name for the following compound?

A) 1,1,2-Trimethyl-1,3-hexenone
B) 1,2-Dimethyl-1,3-hexenone
C) 2,3-Dimethyl-1,3-heptenone
D) 2,3-Dimethyl-2-hepten-4-one
E) 5,6-Dimethyl-5-hepten-4-one

Question 8

What is the correct structure for 7-bromo-1-octyn-4-one?

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

Question 9

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

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

Question 10

A correct name for the following compound would be which of those below?

A) 2,5-Dimethyl-6-hexanal
B) 2,5-Dimethylhexanal
C) 2-Aldehydoisohexane
D) 3,5-Dimethylheptanone
E) 1-Hydro-2,5-dimethyl-1-hexanone

Question 11

Which is the proper name for the structure shown?

A) 2-Chloro-5-aldehydotoluene
B) 6-Chloro-3-aldehydotoluene
C) 2-Methyl-4-aldehydochlorobenzene
D) 4-Chloro-3-methylbenzaldehyde
E) 4-Methyl-5-chloro-2-benzaldehyde

Question 12

What is the correct structure for 2,3-dimethyl-2-hepten-4-one?

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

Question 13

What is the correct IUPAC name for the following compound?

A) 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 14

What is the correct 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 correct structure for 3-phenylpropanal?

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

Question 16

What is the correct IUPAC name for the following compound?

A) 5,5-Dimethyl-2-heptanone
B) 5-Ethyl-5,5-dimethyl-Methyl-2-octanone
C) 5,5-Dimethylcycloheptanone
D) 4,4-Dimethylcycloheptanone
E) 3,3-Dimethylcycloheptanone

Question 17

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

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

Question 18

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

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

Question 19

What is the correct structure for 2,5-dimethylhexanal?

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

Question 20

A correct name for is?

A) 3-Benzylpropanone
B) 3-Phenylpropanal
C) 3-Benzylpropanal
D) Nonanone
E) Nonanal

Question 21

What is the final product,Z,of the following synthesis?

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

Question 22

What is the correct structure for (S)-7-bromo-1-octyn-4-one?

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

Question 23

Which is the IUPAC name for the structure shown below?

A) (R)-5-Bromo-2-heptanal
B) (S)-5-Bromo-2-heptanal
C) (R)-5-Bromo-2-heptanone
D) (S)-5-Bromo-2-heptanone
E) (R)-3-Bromopentyl methyl ketone

Question 24

What is the correct structure for (R)-7-bromo-1-octyn-4-one?

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

Question 25

Select the structure of the major product in the following reaction.

A) Ethylbenzene
B) 1-Phenylethanol
C) Acetophenone
D) 2-Phenylethanal
E) Vinylbenzene

Question 26

Which of the compounds listed below would you expect to have the highest boiling point? (They all have approximately the same molecular weight. )

A) Pentane
B) 1-Butanol
C) Butanal
D) 1-Fluorobutane
E) Diethylether

Question 27

What is the correct structure for (R)-5-bromo-2-heptanone?

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

Question 28

What is the correct structure for (S)-5-bromo-2-heptanone?

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

Question 29

Which is the IUPAC name for the structure shown below?

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 30

Which is the proper name for the structure shown below?

A) 7-Bromo-1,4-octynal
B) 7-Bromo-1,4-octynone
C) 2-Bromo-5,7-octynal
D) 7-Bromo-7-methyl-1-heptyne-3-ketone
E) 7-Bromo-1-octyn-4-one

Question 31

What is the correct structure for (S)-4-cyclohexyl-3-methyl-2-butanone?

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

Question 32

Select the structure of the major product in the following reaction.

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

Question 33

Which of the following procedures would not yield 3-pentanone as a major product?

A)

B)

C)

D)

E)

Question 34

Which is the proper name for the structure shown?

A) 3,5-Dimethyl-5-(4-chlorobenzyl)-1-pentanal
B) 3-Methyl-5-(4-chlorophenyl)hexanol
C) 3,5-Dimethyl-5-(4-chlorophenyl)-1-pentanaldehyde
D) 3-Methyl-5-(4-chlorophenyl)-hexanaldehyde
E) 3-Methyl-5-(4-chlorophenyl)hexanal

Question 35

What is the IUPAC name for ?

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 36

What is the correct structure for (S)-4-cyclohexyl-3-methyl-2-butanone?

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

Question 37

Which is the IUPAC name for the structure shown below?

A) (R)-5-Bromo-2-heptanal
B) (S)-5-Bromo-2-heptanal
C) (R)-5-Bromo-2-heptanone
D) (S)-5-Bromo-2-heptanone
E) (R)-3-Bromopentyl methyl ketone

Question 38

Identify the reagent(s)that would bring about the following reaction: CH₃CH₂CH₂COCl -- $\rightarrow$ CH₃CH₂CH₂CHO

A) H₂/Ni
B) Li/liq.NH₃
C) LiAlH[OC(CH₃)₃]₃,ether
D) NaBH₄,CH₃OH
E) LiAlH₄,ether

Question 39

LiAlH₄ (LAH)cannot be used to convert carboxylic acids to the corresponding aldehydes because:

A) LAH is not sufficiently reactive.
B) RCOOH is converted into RCOOLi.
C) RCOOH is reduced to RCH₂OH.
D) RCOOH is reduced to RCH₃.
E) RCOOH is converted into R₂C=O.

Question 40

What is the correct structure for 4-(1-methylcyclohexyl)-2-butanone?

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

Question 41

Select the structure of the major product in the following reaction.

A) 4-Methylhexanal
B) 4-Methyl-1-hexanol
C) 3-Methylhexanal
D) 4,10-Dimethyldodecane-6,7-dione
E) 4,10-Dimethyldodecane-6,7-diol

Question 42

Select the structure of the major product in the following reaction.

A) 4-Methylhexanal
B) 4-Methyl-1-hexanol
C) 3-Methylhexanal
D) 4,10-Dimethyldodecane-6,7-dione
E) 4,10-Dimethyldodecane-6,7-diol

Question 43

Select the structure of the major product in the following reaction.

A) 3-Methylhexanal
B) 4-Methyl-1-hexanol
C) 4-Methylhexanal
D) 4,10-Dimethyldodecane-6,7-dione
E) 4,10-Dimethyldodecane-6,7-diol

Question 44

A good synthesis of

A) I
B) II
C) III
D) IV
E) All of these are equally useful.

Question 45

A good synthesis of

A) I
B) II
C) III
D) IV
E) All of these are equally useful.

Question 46

Select the structure of the major product in the following reaction.

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

Question 47

Select the structure of the major product in the following reaction.

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

Question 48

A good synthesis of

A) I
B) II
C) III
D) IV
E) All of these are equally useful.

Question 49

A good synthesis of

A) I
B) II
C) III
D) IV
E) All of these are equally useful.

Question 50

Select the structure of the major product in the following reaction.

A) 4-Methylhexanal
B) 4-Methyl-1-hexanol
C) 3-Methylhexanal
D) 4,10-Dimethyldodecane-6,7-dione
E) 4,10-Dimethyldodecane-6,7-diol

Question 51

Select the structure of the major product in the following reaction.

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

Question 52

Which synthesis or syntheses would yield propanal?

A)

B)

C)

D) All of these
E) None of these

Question 53

Which of the following would yield 3-pentanone as the major product?

A)

B)

C)

D) Two of these
E) All of these

Question 54

A good synthesis of

A) I
B) II
C) III
D) IV
E) All of these are equally useful.

Question 55

What would be the product of the following reaction sequence?

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

Question 56

A good synthesis of

A) I
B) II
C) III
D) IV
E) All of these are equally useful.

Question 57

Which of the following is a synthesis of 3-heptanone?

A)

B)

C)

D)

E) All of the above are syntheses of 3-heptanone.

Question 58

Select the structure of the major product in the following reaction.

A) cyclopentanol
B) 1-cyclopentylcyclopentane
C) cyclopentanone
D) cyclopentene
E) 1-(1-hydroxycyclopentyl)-1-hydroxycyclopentane

Question 59

Select the structure of the major product in the following reaction.

A) Ethylbenzene
B) 1-Phenylethanol
C) Acetophenone
D) 2-Phenylethanal
E) Vinylbenzene

Question 60

Which of the following is not a synthesis of benzophenone,

A)

B)

C)

D)

E) All of the above will give benzophenone.

Question 61

Which compound is an acetal?

A) I
B) II
C) III
D) IV
E) All of the above

Question 62

The product,D,of the following sequence of reactions would be:

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

Question 63

The product,E,of the following reaction sequence, would be:

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

Question 64

The product,K,of the following sequence of reactions would be:

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

Question 65

What,in general,is the order of increasing reactivity of these carbonyl compounds towards nucleophilic reagents?

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

Question 66

The product,K,of the following sequence of reactions would be:

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

Question 67

Which compound is a hemiacetal?

A) I
B) II
C) III
D) IV
E) All of the above

Question 68

What is the final product of this synthetic sequence?

A)

B) p-BrC₆H₄CH₂C₆H₅
C) C₆H₅CH₂COOH
D)

E) C₆H₅CH₂C₆H₅

Question 69

What would be the product of the following reaction sequence?

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

Question 70

What would be the product of the following reaction sequence?

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

Question 71

Which of these will not catalyze the reaction of a weak nucleophile with the carbonyl group of an aldehyde or ketone?

A) I^-
B) H₃O⁺
C) AlCl₃
D) BF₃
E) ZnCl₂

Question 72

Which of the following compounds is an acetal?

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

Question 73

What new compound will eventually be formed when HCl is added to a solution of pentanal in methanol?

A)

B)

C)

D)

E)

Question 74

The product,E,of the following reaction sequence, would be:

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

Question 75

What would be the product of the following reaction sequence?

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

Question 76

What would be the product of the following reaction sequence?

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

Question 77

Acetals are unstable in the presence of an aqueous solution of which of these?

A) HCl
B) NaOH
C) KHCO₃
D) Na₂CO₃
E) NaCl

Question 78

What would be the product of the following reaction sequence?

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

Question 79

Which is the general formula for a thioacetal?

A)

B)

C)

D)

E)

Question 80

What,in general,is the order of decreasing reactivity of these carbonyl compounds towards nucleophilic reagents?

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