Deck 16: Reactions of Aldehydes and Ketones

Question 1

Give the common name for the structure.

A)ethyl isobutyl ketone
B)tert-butyl ethyl ketone
C)sec-butyl ethyl ketone
D)ethyl isopropyl ketone
E)isobutyl methyl ketone

Answer 1

ethyl isobutyl ketone

Question 2

Which of the following compounds is benzaldehyde?

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

Answer 2

IV

Question 3

Which of the following compounds is an aldehyde?

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

Answer 3

IV

Question 4

Provide the proper IUPAC name for PhCH₂CH(CH₃)CH₂CH₂CHO.

Question 5

What is the common name for the following compound?

A)chloroaldehyde
B)α-chloroacetaldehyde
C)β-chloroacetaldehyde
D)2-chloroethanal
E)α-chloroethanal

Question 6

Name the structure.

Question 7

Give the best name for the structure.

A)1-oxo-2-butanone
B)1,3-dioxobutane
C)3-oxobutanal
D)3-oxobutanol
E)1-oxo-2-propanone

Question 8

What is the IUPAC name for the following compound?

A)2-bromobutanal
B)α-bromobutanal
C)3-bromobutanal
D)β-bromobutyraldehyde
E)3-bromobutanone

Question 9

Would you expect the carbonyl carbon of benzaldehyde to be more or less electrophilic than that of acetaldehyde? Explain using resonance structures.

Question 10

Provide the IUPAC name for the organic compound below.

Question 11

Provide the IUPAC name for the organic compound below.

Question 12

Provide the systematic name of the compound below.

Question 13

Provide the proper IUPAC name for CH₃CHOHCH₂COCH₂C(CH₃)₂CH₂CH₃.

Question 14

Provide the IUPAC name for the organic compound below.

Question 15

Give the systematic name for the structure.

A)2-methyl-4-hexanone
B)2-methyl-4-heptanone
C)2-methyl-4-pentanone
D)5-methyl-3-hexanone
E)5-methyl-3-heptanone

Question 16

Provide the systematic name of the compound below.

Question 17

What is the IUPAC name for the following compound?

A)5-chloro-3-methylhexanone
B)1-chloro-1,3-dimethyl-4-pentanone
C)5-chloro-3,5-dimethyl-2-pentanone
D)5-chloro-3-methyl-2-hexanone
E)2-chloro-4-methyl-5-hexanone

Question 18

Which of the following compounds is a ketone?

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

Question 19

Which of the following is cyclohexanone?

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

Question 20

Which of the following compounds is acetone?

A)
B)
C)
D)
E)

Question 21

Which of the following most typically characterizes the reactions of aldehydes and ketones?

A)electrophilic addition
B)electrophilic substitution
C)nucleophilic acyl substitution
D)nucleophilic addition
E)radical addition

Question 22

Which carbonyl is more susceptible to nucleophilic attack,that of cyclohexanone or that of hexanal? Provide two reasons for your choice.

Question 23

Which of the following reactions can be used to prepare

A)I
B)II
C)III
D)B and C
E)A,B and C

Question 24

Which of the following alcohols can be prepared by the reaction of methyl formate with excess Grignard reagent?

A)1-pentanol
B)2-pentanol
C)3-pentanol
D)2-methyl-2-pentanol
E)3-methyl-3-pentanol

Question 25

What is the major product when (CH₃)₂CHCH₂CH₂Br is subjected to the following reaction sequence: 1.Mg,ether 2.CO₂ 3.H₃O⁺ ?

A)3-methyl-1-butanol
B)2-methyl-2-butanol
C)4-methyl-1-pentanol
D)4-methylpentanoic acid

Question 26

Which enantiomer is formed from attack of a methyl Grignard reagent on the si face of benzaldehyde?

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

Question 27

Give the organic products for the reaction.

Question 28

What reagent can be used to convert benzophenone into triphenylmethanol?

Question 29

Identify the product for the reaction.

A)
B)
C)
D)
E)CH₃CH₂CH₂OH

Question 30

Which of the following reactions can be used to prepare 3-methyl-3-hexanol?

A)
B)
C)
D)A and B
E)A,B,and C

Question 31

List the following carbonyl compounds in order of decreasing reactivity toward nucleophiles: ester,acid chloride,amide,aldehyde,ketone.

Question 32

Why do aldehydes undergo nucleophilic addition reactions while esters undergo nucleophilic acyl substitution reactions?

A)The carbonyl carbon of an ester is more electrophilic than that of an aldehyde.
B)Aldehydes are more sterically hindered than esters.
C)Once the nucleophile adds to an aldehyde,the tetrahedral intermediate is too sterically hindered to eliminate one of the attached groups.
D)The ester carbonyl carbon is sp3 hybridized while the aldehyde carbonyl carbon is sp2 hybridized.
E)Once the nucleophile adds to an aldehyde,neither H- nor R- can be eliminated since they are strongly basic.

Question 33

Give three different sets of reagents (a carbonyl compound and a Grignard reagent)that could be used to prepare the following compound.

Question 34

Give the product for the following reaction.

A)
B)
C)
D)
E)

Question 35

When camphor undergoes nucleophilic attack by CH₃CH₂MgBr,the major product is the one in which the Grignard reagent has added endo.Explain the stereoselectivity observed.Which face of the carbonyl carbon,re or si,was attacked?

Question 36

What is/are the major product(s)of the following reaction?

A)
B)
C)
D)

Question 37

Provide the major organic product of the following.

Question 38

Identify the product for the reaction.

A)
B)CH₃CH₂CH₂OH
C)
D)CH₃CH₂OH
E)

Question 39

Complete the following reaction sequence by supplying the missing information:

Question 40

What two distinct combinations of Grignard reagent and aldehyde could be used to prepare the alcohol below?

Question 41

Provide the major organic product(s)of the reaction below.

Question 42

Give the product of the following reaction.

Question 43

Provide the major organic product(s)of the reaction below.

Question 44

Which of the following is the best method for preparing lactic acid from acetaldehyde?

A)Cl₂; ^-OH; CH₃OH
B)CH₃MgBr; ^-OH
C)KMnO₄; ^-OH
D)HC N; H₃O⁺/heat
E)Cl₂; Mg/ether; ^-OH

Question 45

Diisobutylaluminum hydride (DIBALH)can be used to carry out which of the following conversions?

A)ester to aldehyde
B)carboxylic acid to ester
C)2 alcohol to ketone
D)aldehyde to carboxylic acid
E)ester to ketone

Question 46

Provide the major organic product(s)of the reaction below.

Question 47

Provide the structure of the cyanohydrin that results when 4-heptanone is treated with HCN/KCN.

Question 48

Provide the structure of the cyanohydrin that results when cyclopentanone reacts with HCN.

Question 49

Which of the sequences works best to accomplish the following conversion?

A)1)NaCN,HCl 2.H₂,Pt
B)1)H₂NCH₂MgBr 2.H₃O⁺
C)1)NaNH₂ 2.H₃O⁺
D)1)H₂NNH₂,H⁺ 2.H₃O⁺
E)1)NH₃,H⁺ 2.H₂,Pt

Question 50

Provide the major organic product(s)of the reaction below.

Question 51

Provide the major organic product of the following.

Question 52

Which of the following amines will react with cyclopentanone to form an enamine?

A)CH₃CH₂CH₂CH₂NH₂
B)(CH₃)₃N
C)pyridine
D)(CH₃)₃CNH₂
E)none of the above

Question 53

When the carbonyl group of a neutral ketone is protonated

A)the resulting species becomes more electrophilic.
B)the resulting species is activated toward nucleophilic attack.
C)subsequent nucleophilic attack on the resulting species is said to occur under acid-catalyzed conditions.
D)the resulting species has a positive charge.
E)all of the above.

Question 54

What class of organic compounds results when cyclopentanone reacts with ethylamine in the presence of trace acid?

A)cyanohydrin
B)semicarbazone
C)imine
D)enamine
E)oxime

Question 55

Give the product for the following reaction.

A)CH₃CH₂CH₂CH₂CH₂CH₃
B)
C)CH₃CH₂CH₂CH₂CH₃
D)
E)

Question 56

What is the major product of the following reaction?

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

Question 57

Provide the major organic product which results when (CH₃)₂CHCH₂CH₂COCl is treated with DIBAH.

Question 58

Which of the following reactions is the best method for preparing acetaldehyde?

A)
B)
C)
D)
E)

Question 59

Give the product for the following reaction.

Question 60

Which of the following reagents can be used to reduce acetaldehyde to ethyl alcohol?

A)1)LiAlH₄ 2.H₃O⁺
B)1)NaBH₄ 2.H₃O⁺
C)H₂/Pt
D)A and C
E)A,B,and C

Question 61

What is the major organic product of the following reaction?

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

Question 62

Provide the major organic product of the following.

Question 63

Give the product for the following reaction.

A)
B)
C)
D)
E)

Question 64

Provide a detailed,stepwise mechanism for the acid-catalyzed condensation reaction between cyclohexanone and H₂NOH.

Question 65

Provide a detailed,stepwise mechanism for the acid-catalyzed condensation reaction between benzaldehyde and methylamine.

Question 66

What is the major organic product of the following reaction?

A)
B)
C)
D)
E)

Question 67

Which of the following is an enamine?

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

Question 68

Provide the major organic product(s)of the reaction below.

Question 69

Propose a plausible mechanism that would explain the following conversions:

Question 70

Conversion of aldehydes and ketones to imines is an acid-catalyzed process.Explain why this conversion is actually hindered by the presence of too much acid.

Question 71

Draw the two major resonance forms of the cation which results when cyclohexanone's carbonyl group is protonated.

Question 72

Provide the structure of cyclohexanone oxime.

Question 73

Which of the following compounds is a hydrazone?

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

Question 74

Which would be more appropriate as the reduction in the following sequence,a Clemmensen or a Wolff-Kishner? Explain.

Question 75

What is the major organic product of the following reaction?

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

Question 76

Give the product for the following reaction.

A)CH₃CH₂CH₂NHCH₃
B)
C)
D)CH₃CH₂CH₂CH₃
E)

Question 77

Provide the major organic product(s)of the reaction below.

Question 78

Provide the major organic product of the reaction of aniline with 3-pentanone.

Question 79

Give the product for the following reaction.

A)CH₃CH₂NHCH₃
B)CH₃CH₂CH₂OH
C)
D)CH₃CH₂CH₂NHCH₃
E)CH₃CH₂CH₂N(CH₃)₂

Question 80

Give the product for the following reaction.

A)
B)
C)
D)
E)