Deck 16: Aldehydes and Ketones

Question 1

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

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

Answer 1

II

Question 2

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

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

Answer 2

I

Question 3

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

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

Answer 3

I

Question 4

What is the correct IUPAC name for the following compound?

A)2-Bromobutanone
B)(S)-2-Bromo-cyclobutanone
C)(R)-2-Bromo-cyclobutanone
D)(S)-1-Bromo-2-cyclobutanone
E)(R)-1-Bromo-2-cyclobutanone

Question 5

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 6

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 7

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

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

Question 8

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

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

Question 9

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

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

Question 10

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 11

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

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

Question 12

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 13

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

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

Question 14

What is the correct structure for 3-phenylpropanal?

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

Question 15

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 16

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 17

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

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

Question 18

A correct name for is?

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

Question 19

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 20

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 21

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 22

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 23

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

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

Question 24

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

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

Question 25

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

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

Question 26

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

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

Question 27

What is the correct IUPAC name for the following compound?

A)bicyclo[1.1.1]pentan-2-one
B)bicyclo[1.1.0]pentan-2-one
C)cyclopentanone
D)methylenepentan-2-one
E)bicyclo[1.0.1]pentan-2-one

Question 28

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 29

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 30

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

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

Question 31

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 32

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

Question 33

What is the correct IUPAC name for the following compound?

A)(1S,4R)-bicyclo[2.2.1]hexan-2-one
B)(1S,4R)-bicyclo[2.1.2]heptan-2-one
C)(1S,4R)-bicyclo[2.2.1]heptan-2-one
D)(1R,4S)-bicyclo[2.1.1]heptan-2-one
E)(1S,4S)-bicyclo[2.1.2]heptan-2-one

Question 34

Which is the proper name for the structure shown?

A)3-Methyl-5-(1,4-dinitrobenzyl)-1-pentanal
B)3-Methyl-1-(2,5-dinitrophenyl)-5-pentanal
C)3-Methyl-5-(2,5-dinitrophenyl)pentanal
D)3-Methyl-5-(2,5-dinitrophenyl)pentanaldehyde
E)3-Methyl-5-(2,5-dinitrophenyl)pentaldehyde

Question 35

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

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

Question 36

What is the correct IUPAC name for the following compound?

A)bicyclo[1.1.0]butan-2-one
B)bicyclo[1.0.1]butan-2-one
C)bicyclo[1.1.0]pentan-2-one
D)bicyclo[0.1.1]butan-2-one
E)bicyclo[1.0.1]pentan-2-one

Question 37

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)Diethyl ether

Question 38

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

Question 39

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

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

Question 40

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 41

The following reduction can be carried out with which reagent(s)?

A)Zn(Hg),HCl
B)i)HSCH₂CH₂SH,BF₃ ; ii)Raney Ni (H₂)
C)NaBH₄,CH₃OH
D)Zn(Hg),HCl and i)HSCH₂CH₂SH,BF₃ ; ii)Raney Ni (H₂)
E)Zn(Hg),HCl and NaBH₄,CH₃OH

Question 42

Which reagent(s)could be used to carry out the following transformation?

A)Zn(Hg),HCl,reflux
B)LiAlH₄,ether
C)HSCH₂CH₂SH,BF₃; then Raney Ni (H₂)
D)All of these choices.
E)Two of these choices.

Question 43

The following reduction can be carried out with which reagent(s)?

A)Zn(Hg),HCl
B)i)HSCH₂CH₂SH,BF₃ ; ii)Raney Ni (H₂)
C)H₂NNH₂,KOH
D)None of these choices.
E)All of these choices.

Question 44

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

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

Question 45

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

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

Question 46

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 47

Stereoisomers can exist in the case of which of the following?

A)The hydrazone of butanone
B)The oxime of acetone
C)The phenylhydrazone of cyclohexanone
D)The cyclic acetal formed from propanal and ethane-1,2-diol
E)The imine of cyclopentanone

Question 48

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

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

Question 49

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

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

Question 50

The compound is produced by the reaction of an excess of benzaldehyde with which compound?

A)Ammonia
B)Hydrazine
C)Nitrogen
D)Phenylhydrazine
E)Hydroxylamine

Question 51

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 52

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 53

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

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

Question 54

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

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

Question 55

The migratory aptitude for groups attached to a ketone or aldehyde carbonyl during the Baeyer-Villiger oxidation is:

A)H > Ph- > 3° alkyl > 2° alkyl > 1° alkyl > methyl
B)Ph- > H > 3° alkyl >2° alkyl >1° alkyl > methyl
C)3° alkyl > 2° alkyl > 1° alkyl > methyl > H > Ph-
D)3° alkyl > 2° alkyl > 1° alkyl > methyl > Ph- >H
E)H > 3° alkyl > 2° alkyl > 1° alkyl > methyl >Ph-

Question 56

In which of the following reactions is the final product expected to be formed as a racemic mixture?

A)
B)
C)

D)
E)

Question 57

Stereoisomers can exist in the case of which of the following?

A)The hydrazone of benzophenone
B)The oxime of 2-methylcyclopentanone
C)The phenylhydrazone of 4-methylcyclohexanone
D)The imine of cyclopentanone
E)Two of these choices.

Question 58

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

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

Question 59

Which reagent will not differentiate between 3-butenal and 2-butanone?

A)Br₂/CCl₄
B)Ag₂O,OH^-
C)H₂NNHC₆H₅
D)KMnO₄,OH^-
E)None of these choices.

Question 60

Dissolving benzaldehyde in methyl alcohol establishes an equilibrium with what compound(s)?

A)
B)
C)C₆H₅C(OCH₃)₃
D) and

E) and C₆H₅C(OCH₃)₃

Question 61

What is the major product of the following reaction sequence?

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

Question 62

The product,K,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 sequence of reactions would be:

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

Question 64

What would be the product of the following reaction sequence?

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

Question 65

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

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

Question 66

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

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

Question 67

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

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

Question 68

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

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

Question 69

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

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

Question 70

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

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

Question 71

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

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

Question 72

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

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

Question 73

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

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

Question 74

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 75

What is the major product of the following reaction sequence?

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

Question 76

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

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

Question 77

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

A)
B)CH₃CH₂COOCH₃
C)
D)CH₃CH=CHCOOH
E)None of these choices.

Question 78

What is the major product of the following reaction sequence?

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

Question 79

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

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

Question 80

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

A)
B)CH₃CH₂COOCH₃
C)
D)CH₃CH=CHCOOH
E)