Deck 16: Aldehydes and Ketones

Question 1

What is the common name of the compound shown below?

A)benzene aldehyde
B)benzaldehyde
C)acetaldehyde
D)phenone

Answer 1

B

Question 2

Which compound is an example of a ketone?

A)
B)
C)
D)
E)None of the above structures are ketones.

Answer 2

A

Question 3

Which compound has the highest boiling point?

A)CH₃(CH₂)₅CH₃
B)CH₃(CH₂)₄CHO
C)CH₃(CH₂)₄CH₂OH
D)All of the compounds above have the same boiling point.

Answer 3

C

Question 4

What product is formed when the compound shown below is treated with Tollens reagent?

A)
B)
C)
D)

Question 5

What product is formed when the compound below is oxidized with K₂Cr₂O₇?

A)
B)
C)
D)No reaction occurs.

Question 6

What is the structure of 1-chloro-3-ethyl-2-heptanone?

A)
B)
C)
D)

Question 7

Which compound will give a positive result in a Tollens test?

A)
B)
C)
D)
E)More than one of the compounds above will give a positive Tollens test result.

Question 8

The compound shown below belongs to what class of compounds?

A)alkane
B)aldehyde
C)ketone
D)acetal
E)carboxylic acid

Question 9

Which compound has the greatest solubility in water?

A)CH₃(CH₂)₅CHO
B)CH₃(CH₂)₄COCH₂CH₃
C)CH₃CH₂CHO
D)The compounds above are equally soluble in water.

Question 10

Which compound could be oxidized to form the carboxylic acid below?

A)CH₃(CH₂)₅CHO
B)
C)
D)

Question 11

The Tollens reagent is which of the following?

A)K₂Cr₂O₇
B)H₂SO₄
C)Cl₂
D)Ag₂O in aqueous NH₄OH

Question 12

Which is the structure of 3-bromo-2-methylbutanal?

A)
B)
C)
D)

Question 13

What is the IUPAC name of the compound shown below?

A)1-pentanone
B)cyclopentanone
C)phenone
D)cyclopentone

Question 14

What is the condensed formula of the compound shown below?

A)CH₃CO(CH₂)₃CH(CH₃)₂
B)CH₃CO(CH₂)₃CHCH₃CH₃
C)CH₃OC(CH₂)₃CHCH₃CH₃
D)CH₃OCCH₂CH₂CH₂CH₂CH(CH₃)₂

Question 15

Which compound(s)would give a positive Tollens test?

A)alcohols
B)aldehydes
C)ketones
D)carboxylic acids
E)alcohols and aldehydes

Question 16

What is the structure of 1-chloro-3-ethyl-2-heptanone?

A)
B)
C)
D)

Question 17

What is the IUPAC name of the compound shown below?

A)methyl hexyl ketone
B)6, 6-dimethyl-2-hexanone
C)6-methyl-2-heptanone
D)2-methyl-6-heptanone

Question 18

What is the IUPAC name of the compound shown below?

A)5-chloro-3-methylhexanal
B)2-chloro-4-methylhexanal
C)5-chloro-3-methyl-6-hexanal
D)2-chloro-4-methylhexanone
E)3-chloro-5-methylhexanone

Question 19

Which compound is soluble in heptane, but not soluble in water?

A)(CH₃)₂CH(CH₂)₅CHO
B)CH₃COCH₃
C)CH₃CH₂CHO
D)All of the compounds above are soluble in both heptane and water.

Question 20

Which of the following represents the general condensed formula for an aldehyde?

A)RCOOH
B)RCHO
C)RCOR
D)RCOH
E)RCH₂OH

Question 21

What is the name of the compound below?

A)2-ethylbenzenone
B)2-ethylacetophenone
C)2-ethylacetobenzone
D)2-ethylphenone

Question 22

What is the product of the reduction of a ketone?

A)a primary alcohol
B)a secondary alcohol
C)a tertiary alcohol
D)a carboxylic acid
E)an ether

Question 23

What hemiacetal is formed in the reaction below?

A)
B)
C)
D)

Question 24

The compound below is classified as what type of compound?

A)an acetal
B)a hemiacetal
C)an ether
D)an acetal and an ether

Question 25

What type of compound is shown below?

A)an epoxide
B)a cyclic hemiacetal
C)an aldehyde
D)a cyclic acetal

Question 26

What is the name of the compound below?

A)3-bromo-4-ethyl-2-methylbenzaldehyde
B)3-bromo-4-ethoxy-2-methoxybenzaldehyde
C)1-bromo-2-ethoxy-6-methoxy-3-benzaldehyde
D)3-bromo-4-ethoxy-2-methoxyphenal

Question 27

What is the structure of 3-hydroxy-2-methylbenzaldehyde?

A)
B)
C)
D)

Question 28

The compound below is classified as what type of compound?

A)an acetal
B)a hemiacetal
C)an ether
D)a cyclic acetal
E)an acetal and an ether

Question 29

What is the IUPAC name of the compound below?

A)4-chloro-3-pentyl-1-cyclohexone
B)4-chloro-3-pentylcyclohexanone
C)1-chloro-2-pentyl-4-cyclohexanone
D)4-chloro-3-pentylphenone

Question 30

What is the structure of 3-hydroxy-2-methylbenzaldehyde?

A)
B)
C)
D)

Question 31

What reaction does the coenzyme NADH, in the presence of an enzyme, facilitate?

A)the reduction of a carbonyl group to form a carboxylic acid
B)the reduction of a carbonyl group to form an alcohol
C)the reduction of a carboxylic acid to form a carbonyl group
D)the oxidation of a carbonyl group to form an alcohol
E)the oxidation of a carbonyl group to form a carboxylic acid

Question 32

What type of compound is shown below?

A)an epoxide
B)a cyclic hemiacetal
C)an aldehyde
D)a cyclic acetal

Question 33

What is the acetal formed in the reaction below?

A)
B)
C)
D)

Question 34

What hydrolysis products are formed when the acetal (CH₃CH₂CH₂)₂C(OCH₂CH₃)₂ is treated with H₂SO₄ in H₂O?

A)(CH₃CH₂CH₂)₂CHOCH₂CH₃ + CH₃CH₂OH
B)(CH₃CH₂CH₂)₂CO + 2 CH₃CH₂OH
C)(CH₃CH₂CH₂)₂CHOH + 2 CH₃CH₂OH
D)CH₂(OCH₂CH₃)₂ + 2 CH₃CH₂CH₃

Question 35

Which compound is a hemiacetal?

A)
B)
C)
D)
E)

Question 36

Which compound is an acetal?

A)
B)
C)
D)
E)

Question 37

A hemiacetal contains which two groups bonded to the same carbon atom?

A)an OH (hydroxyl)group and an OR (alkoxy)group
B)two OH (hydroxyl)groups
C)two OR (alkoxy)groups
D)an OH (hydroxyl)group and a C=O (carbonyl)group

Question 38

What is the name of the compound below?

A)2-ethylbenzenone
B)2-ethylacetophenone
C)2-ethylacetobenzone
D)2-ethylphenone

Question 39

Which reagent can be used to reduce a ketone?

A)K₂Cr₂O₇
B)H₂SO₄
C)H₂ with Pd metal
D)Ag₂O in aqueous NH₄OH

Question 40

What is the product of the reduction of an aldehyde?

A)a primary alcohol
B)a secondary alcohol
C)a tertiary alcohol
D)a carboxylic acid
E)an ether

Question 41

The reaction below illustrates oxidation by Tollens' reagent.

Question 42

Salicin is a naturally occurring pain reliever isolated from the bark of willow trees. Which statement concerning the functional groups present in salicin is incorrect?

A)It contains an acetal.
B)It contains an alcohol.
C)It contains a hemiacetal.
D)It contains a phenol.

Question 43

The following ketones play an important role in the tanning industry and are found in many commercial sunscreens. Which ketone is expected to be the most soluble in water and therefore the most readily washed off when an individual goes swimming?

A)
B)
C)
D)All would be expected to have the same solubility.

Question 44

Salicin is a naturally occurring pain reliever isolated from the bark of willow trees. Which statement concerning the functional groups present in salicin is incorrect?

A)It contains an acetal.
B)It contains an alcohol.
C)It contains a hemiacetal.
D)It contains a phenol.

Question 45

The reduction of acetaldehyde is an important biochemical reaction. Which of the following is the product of its reduction?

A)
B)
C)
D)

Question 46

The following ketones play an important role in the tanning industry and are found in many commercial sunscreens. Which ketone is expected to be the most soluble in water and therefore the most readily washed off when an individual goes swimming?

A)
B)
C)
D)All would be expected to have the same solubility.

Question 47

When light hits the retina, the 11-cis double bond of 11-cis-retinal is isomerized to its more stable trans isomer, and the all-trans-retinal is formed.

Question 48

Acetals are ethers.

Question 49

The compound below is an acetal.

Question 50

What is the name of the compound below?

A)3-bromo-4-ethyl-2-methylbenzaldehyde
B)3-bromo-4-ethoxy-2-methoxybenzaldehyde
C)1-bromo-2-ethoxy-6-methoxy-3-benzaldehyde
D)3-bromo-4-ethoxy-2-methoxyphenal

Question 51

Aldehydes and ketones undergo addition reactions with alcohols (ROH)to form hemiacetals and acetals.

Question 52

The compound butanone does not need a number to specify the location of the carbonyl group on the carbon chain. Which statement best explains why?

A)The C=O is assumed to be on C-1 of the carbon chain if it is not specified.
B)The C=O can only be on C-2 of the carbon chain in this compound.
C)The location of the C=O does not need to be specified for a cyclic ketone.
D)The C=O is on an end carbon of the carbon chain.

Question 53

The reaction below illustrates oxidation by Tollens reagent.

Question 54

The compound decanal contributes to the odor and flavor of an orange. Which of the statements concerning the structure of decanal is incorrect?

A)Decanal is an aldehyde.
B)Decanal contains a saturated chain of ten carbons.
C)Decanal contains a carbonyl group on the first carbon of the carbon chain.
D)Decanal is an aromatic compound.

Question 55

Aldehydes and ketones undergo addition reactions with alcohols (ROH)to form hemiacetals and acetals.

Question 56

What product results when cinnamaldehyde is oxidized?

A)
B)
C)
D)

Question 57

The reduction of acetaldehyde is an important biochemical reaction. Which of the following is the product of its reduction?

A)
B)
C)
D)

Question 58

As is in the laboratory, the reduction of carbonyl groups in biological systems is accomplished using H₂ and Pd as a reducing agent.

Question 59

When the hemiacetal below reacts with ethanol, what acetal is formed?

A)
B)
C)
D)

Question 60

What product results when cinnamaldehyde is oxidized?

A)
B)
C)
D)

Question 61

Triamcinolone acetonide (structure shown), a synthetic corticosteroid drug, contains an acetal.

Question 62

When the compound shown is treated with H₂ and a Pd catalyst, the indicated product is formed.

Question 63

The carbohydrate glucose exists predominantly as a cyclic hemiacetal.

Question 64

Vanillin, acetone, and formaldehyde are aldehydes.

Question 65

Oxidation of the aldehyde below gives the indicated product.

Question 66

The IUPAC name of the compound below is 2-methyl-2-propylpropanal.

Question 67

Acetals are stable molecules, but they can be converted back to aldehydes and ketones by treatment with acid and water.

Question 68

When acetaldehyde is reduced by the addition of hydrogen, ethanol is produced.

Question 69

Cyclic hemiacetals are converted to acetals by reaction with an alcohol.

Question 70

The IUPAC name of the molecule below is 3-ethoxy-3-propoxy-7-heptanal.

Question 71

The compound below is soluble in water and in hexane.

Question 72

Triamcinolone acetonide (structure shown), a synthetic corticosteroid drug, contains an acetal.

Question 73

The ketone below produces the indicated product upon oxidation with K₂Cr₂O₇.

Question 74

When 3-heptanone is treated with 2 equivalents of 1-butanol in the presence of sulfuric acid, the product is the compound shown below.

Question 75

When the compound shown is treated with H₂ and a Pd catalyst, the indicated product is formed.

Question 76

Ketones are not oxidized since they contain no H atom bonded to the carbonyl carbon.

Question 77

The reaction below illustrates oxidation of an aldehyde.

Question 78

The ketone below produces the indicated product upon oxidation with K₂Cr₂O₇.

Question 79

D-Glucose, shown below, will give a positive Tollens test.

Question 80

The reaction below illustrates oxidation of an aldehyde.