Deck 20: Aldehydes and Ketones

Question 1

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

Answer 1

Question 2

What is the IUPAC name for the following compound?

Answer 2

5,5-dimethyl-2-heptanone

Question 3

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

Answer 3

3-phenylpropanal

Question 4

What is the IUPAC name for the following compound?

Question 5

What is the IUPAC name for the following compound?

Question 6

Provide the structure for 4-methylbenzaldehyde.

Question 7

Provide the structure for m-nitroacetophenone.

Question 8

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

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

Question 9

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 10

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 11

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 12

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

Question 13

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 14

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

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

Question 15

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 16

What is the IUPAC name for the following compound?

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)-2-bromo-6-heptanone

Question 17

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

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

Question 18

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 19

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

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

Question 20

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 21

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

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

Question 22

Predict the product for the following reaction

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

Question 23

Predict the product for the following reaction.

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

Question 24

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 25

Predict the product for the following reaction.

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

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?

Question 28

Predict the product for the following reaction

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

Question 29

Provide the structure for benzophenone.

Question 30

Predict the product for the following reaction

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

Question 31

Predict the product for the following conversion.

Question 32

Predict the product for the following reaction.

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

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

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 36

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 37

Predict the major product for the following reaction

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

Question 38

Predict the product(s)for the following reaction.

Question 39

Predict the product for the following reaction.

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

Question 40

Predict the product for the following reaction.

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

Question 41

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 42

Provide the product for the following reaction

A)3-methylhexane
B)3-methyl-4-hexanol
C)4-methyl-2-hexene
D)3-methyl-4-hexene
E)3-methyl-3-hexene

Question 43

Predict the product for the following reaction.

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

Question 44

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

Question 45

Predict the product for the following reaction.

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

Question 46

Predict the product for the following reaction.

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

Question 47

Provide the product for the following reaction

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

Question 48

Predict the product,when pentanal reacts with methanamine in presence of acid catalyst.

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

Question 49

Predict the product of the following reaction.

Question 50

Predict the product of the following reaction.

Question 51

Predict the product for the following reaction

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

Question 52

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

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

Question 53

Predict the product for the following reaction.

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

Question 54

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

Question 55

Predict the product for the following reaction.

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

Question 56

Which reagent(s)could NOT be used to carry out the following transformation?

A)Zn(Hg),HCl
B)LiAlH₄,ether
C)HSCH₂CH₂SH,BF₃;then Raney Ni (H₂)
D)NH₂NH₂/KOH/heat

Question 57

Provide the reactant(s)necessary to prepare the following compound.

Question 58

Predict the product for the following reaction sequence.

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

Question 59

Predict the product,when cyclopentanecarbaldehyde reacts with phenylhydrazine in presence of acid catalyst.

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

Question 60

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

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

Question 61

Predict the product of the following reaction sequence.

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

Question 62

Which one of the following compounds gives 5-methyl-3-heptanol with LiAlH₄ followed by water?

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

Question 63

Predict the product for the following reaction sequence.

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

Question 64

Provide the structure of the reactants necessary to prepare the following compound using Wittig reaction.

Question 65

Provide the structure of the reactant in the following reaction.

A)cyclohexanone
B)cyclohexanecarbaldehyde
C)cyclohexylpropanone
D)3-cyclohexylpropanal

Question 66

Which one of the following compounds will yield 1-hexanol when treated with butylmagnesium bromide followed by acid workup?

A)1-hexanol
B)formaldehyde
C)acetaldehyde
D)oxirane
E)hexanal

Question 67

What is the correct order of migration rate for the following groups in the Baeyer-Villiger oxidation reaction?

A)phenyl > methyl > t-butyl > H
B)phenyl > t-butyl > methyl > H
C)H > phenyl > methyl > t-butyl
D)H > phenyl > t-butyl > methyl
E)methyl > t-butyl > phenyl > H

Question 68

Suggest a stepwise synthesis of 1-pentanol from 1-butanal

Question 69

Provide the product of the following reaction.

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

Question 70

Predict the product of the following reaction sequence.

Question 71

Provide the product for the following reaction sequence.

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

Question 72

Predict the product of the following reaction sequence.

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

Question 73

Provide the structure of the ylide needed to prepare 3-ethyl-3-heptene from 3-pentanone using a Wittig reaction.

A)Ph₃P=CH(CH₂CH₃)₂
B)Ph₃P=CHCH₂CH₃
C)Ph₃P=CHCH₂CH₂CH₃
D)Ph₃P=CH₂
E)Ph₃P=CHCH₂(CH₃) ₂

Question 74

Suggest a stepwise synthesis of 1-pentanal from 1-butanal..

Question 75

Provide the structure for X,Y and Z,for the following reaction sequence.

Question 76

Provide the major product for the following reaction sequence.

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

Question 77

Predict the product for the following reaction.

Question 78

Predict the product for the following reaction sequence.

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

Question 79

What would be the product of the following reaction?

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

Question 80

Suggest a stepwise synthesis of 1-phenylpropanal from benzyl alcohol..