CHAPTER 15

Aldehydes and Ketones

Test Bank

TYPE I MULTIPLE-CHOICE QUESTIONS

In each of the following multiple-choice questions, place the letter of the correct response in the blank
at the left. There is only one correct response for each question.

15.1 c Which of the following structural features is common to both aldehydes and ketones?

O
a) C OH

O
b) C H

O
c) C

O
d) C OR

15.2 a Which of the following structural features is possessed by aldehydes but not ketones?
a) At least one hydrogen atom is bonded to the carbonyl carbon atom.
b) At least one hydroxyl group is bonded to the carbonyl carbon atom.
c) The carbonyl carbon atom is bonded to two other carbon atoms.
d) The carbonyl carbon atom is part of a ring structure.

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Test Bank Chapter 15: Aldehydes and Ketones 165

15.3 b [Algorithmic]Which of the following statements concerning aldehydes and ketones

is correct?
a) Cyclic aldehydes, but not cyclic ketones, exist.
b) Cyclic ketones, but not cyclic aldehydes, exist.
c) Both cyclic aldehydes and cyclic ketones exist.
d) Neither cyclic aldehydes nor cyclic ketones exist.

15.4 b The simplest aldehyde and ketone contain, respectively, how many carbon atoms?
a) 1 and 1
b) 1 and 3
c) 2 and 2
d) 2 and 3
O
15.5 d The IUPAC name for the compound CH3 CH2 C H is
a) acetaldehyde.
b) propionaldehyde.
c) 1-ethanal.
d) propanal.
O CH3
15.6 c The IUPAC name for the compound CH3 C CH2 CH CH3 is
a) 2-methyl-2-pentanone.
b) 2-methyl-4-pentanone.
c) 4-methyl-2-pentanone.
d) 2-methyl-4-pentaketone.

15.7 a [Algorithmic]What is the IUPAC name of the aldehyde whose common name is
formaldehyde?
a) methanal
b) ethanal
c) propanal
d) 2-methylpropanal

15.8 c Two other acceptable names for the compound acetone are
a) propanone and diethyl ketone.
b) ethanone and methyl ethyl ketone.
c) propanone and dimethyl ketone.
d) ethanone and diethyl ketone.

15.9 c How many saturated noncyclic six-carbon ketones are there?

a) two
b) four
c) six
d) eight

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166 Chapter 15: Aldehydes and Ketones Test Bank

15.10 d What two functional groups are never found at the end of a carbon chain?
a) alcohol and aldehyde
b) ether and aldehyde
c) alcohol and ketone
d) ether and ketone

15.11 d [Algorithmic]Which of the following statements concerning hydrogen bonding is

correct?
a) Ketone molecules can hydrogen bond to each other.
b) Aldehyde molecules can hydrogen bond to each other.
c) Both ketone molecules and aldehyde molecules can hydrogen bond to each
other.
d) Neither ketone molecules nor aldehyde molecules can hydrogen bond to each
other.

15.12 d [Algorithmic]Comparison of the boiling points of aldehydes and ketones with those
of other compounds of similar molecular mass shows that they are
a) lower than those of alcohols and alkanes.
b) higher than those of alcohols and alkanes.
c) higher than those of alcohols but lower than those of alkanes.
d) higher than those of alkanes but lower than those of alcohols.

15.13 b Ketones may be prepared by the oxidation of

a) primary alcohols.
b) secondary alcohols.
c) tertiary alcohols.
d) aldehydes.

15.14 a [Algorithmic]Which of the following statements concerning the oxidation of

aldehydes and ketones is correct?
a) Aldehydes readily undergo oxidation and ketones are resistant to oxidation.
b) Ketones readily undergo oxidation and aldehydes are resistant to oxidation.
c) Both aldehydes and ketones readily undergo oxidation.
d) Both aldehydes and ketones are resistant to oxidation.

15.15 a The oxidizing agent in the Tollen’s test for the presence of an aldehyde is
a) Ag+
b) Ag
c) Cu2+
d) Cu2O

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Test Bank Chapter 15: Aldehydes and Ketones 167

O
15.16 a What is the product when CH3 C CH3 is reduced using H2 gas and a Ni catalyst?

OH
a) CH3 CH CH3

OH
b) CH2 C CH3

O
c) CH3 C H

d) CH 2 CH CH3

15.17 c When an alcohol molecule adds across a carbon-oxygen double bond of an aldehyde
or ketone, the
a) H atom from the alcohol bonds to the carbonyl carbon atom.
b) OH portion from the alcohol bonds to the carbonyl oxygen atom.
c) OR portion from the alcohol bonds to the carbonyl carbon atom.
d) OH portion from the alcohol bonds to the carbonyl carbon atom.

15.18 a A hemiacetal is a compound in which

a) a hydroxy group and an alkoxy group are attached to the same carbon atom.
b) a hydroxyl group and an alkoxy group are attached to adjacent carbon atoms.
c) two alkoxy groups are attached to the same carbon atom.
d) two alkoxy groups are attached to adjacent carbon atoms.

15.19 a The structural difference between a hemiacetal and an acetal is the replacement of a
a) –OH group with an –OR group.
b) H atom with an –OR group.
c) H atom with a –OH group.
d) –OR group with a –OH group.

15.20 d Hydrolysis of an acetal in an acid solution would yield

a) an aldehyde, a ketone, and one alcohol.
b) an aldehyde, a ketone, and two alcohols.
c) an aldehyde or a ketone and one alcohol.
d) an aldehyde or a ketone and two alcohols.

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168 Chapter 15: Aldehydes and Ketones Test Bank

TYPE II MULTIPLE-CHOICE QUESTIONS

In each of the following multiple-choice questions, place the letter of the correct response in the blank
at the left. There may be more than one correct response for a question (choice d) or no correct
response for a question (choice e).

15.21 b Which of the following statements concerning a carbonyl group is incorrect?

a) It is polar.
b) It contains two oxygen atoms and one carbon atom.
c) It is present in both aldehydes and ketones.
d) more than one correct response
e) no correct response

15.22 d Which of the following is a correct notation for the aldehyde functional group?

a) CHO

O
b) C H

O
c) C

d) more than one correct response

e) no correct response

15.23 a Which of the following aldehydes is paired with an incorrect IUPAC name?

Cl O
a) CH3 CH CH2 C H ; 2-chloro-4-butanal

Cl O
b) CH3 CH2 CH C H ; 2-chlorobutanal

Cl Cl O
c) CH3 CH CH C H ; 2,3-dichlorobutanal

d) more than one correct response

e) no correct response

15.24 b Which of the following pairings of aldehyde common and IUPAC names is correct?
a) acetaldehyde and methanal
b) 2-methylbutyraldehyde and 2-methylbutanal
c) formaldehyde and ethanal
d) more than one correct response
e) no correct response

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Test Bank Chapter 15: Aldehydes and Ketones 169

15.25 c Which of the following pairings of ketone IUPAC and common names is correct?
a) 2-methyl-3-pentanone and methyl propyl ketone
b) 3-methyl-2-pentanone and isopropyl methyl ketone
c) propanone and dimethyl ketone
d) more than one correct response
e) no correct response

15.26 d Which of the following compounds is a constitutional isomer of 2-pentanone?

a) 3-methyl-2-pentanone
b) 3-methyl-2-butanone
c) isopropyl methyl ketone
d) more than one correct response
e) no correct response

15.27 a Which of the following compounds contains 7 carbon atoms?

a) benzaldehyde
b) acetophenone
c) benzophenone
d) more than one correct response
e) no correct response

15.28 b In which of the following pairs of compounds does the first listed compound have a
greater water solubility than the second listed compound?
a) butanal, methanal
b) propanone, 2-pentanone
c) hexanal, 2-butanone
d) more than one correct response
e) no correct response

15.29 b Oxidation of which of the following alcohols will produce a ketone?

a) CH3 CH2 OH

b) CH3 CH CH3
OH

CH3
c) CH3 C OH
CH3

d) more than one correct response

e) no correct response

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170 Chapter 15: Aldehydes and Ketones Test Bank

15.30 c Which of the following compounds would be resistant to oxidation with a mild
oxidizing agent?
a) CH3 CH2 CH2 OH

O
b) CH3 CH2 C H

O
c) CH3 C CH3

d) more than one correct response

e) no correct response

15.31 d Hydrogenation, with a catalyst, of which of the following compounds would produce
a four-carbon alcohol?
a) butanal
b) 2-butanone
c) diethylketone
d) more than one correct response
e) no correct response

15.32 a In which of the following pairings of compound types does the first listed compound
type contain more alkoxy groups than the second listed compound type?
a) acetal, hemiacetal
b) hemiacetal, acetal
c) aldehyde, hemiacetal
d) more than one correct response
e) no correct response

15.33 a Which of the following is a product of the acid hydrolysis of the following
compound?
OH
CH3 CH2 C H
O CH3

a) methyl alcohol
b) ethyl alcohol
c) propanone
d) more than one correct response
e) no correct response

15.34 d Which of the following types of compounds contains a carbon-sulfur double bond?
a) a thial (thioaldehyde)
b) a thione (thioketone)
c) a sulfoxide
d) more than one correct response
e) no correct response

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Test Bank Chapter 15: Aldehydes and Ketones 171

15.35 c Which of the following compounds would be named as a ketone?

OH O
a) CH3 CH CH2 C H

O O
b) CH3 C CH2 C H

OH O
c) CH3 CH CH2 C CH3

d) more than one correct response

e) no correct response

MULTIPLE-CHOICE FORMAT TRUE-FALSE QUESTIONS

In each of the following multiple-choice questions, characterize EACH of the three given statements
as being TRUE or FALSE and then indicate the collective true-false status of the statements using the
choices a) All three statements are true.
b) Two of the three statements are true.
c) Only one of the statements is true.
d) None of the statements is true.

15.36 b - TTF Statements:

(1) Cyclic hemiacetals are usually more stable than noncyclic hemiacetals.
(2) A carbonyl group consists of a carbon atom and an oxygen atom joined by a
double bond.
(3) The compound benzaldehyde contain six carbon atoms.
a) All three statements are true.
b) Two of the three statements are true.
c) Only one of the statements is true.
d) None of the statements is true.

15.37 a - TTT Statements:

(1) The simplest aldehyde is formaldehyde and the simplest ketone is acetone.
(2) Carbonyl group polarity makes dipole-dipole interactions between like
aldehyde molecules or like ketone molecules possible.
(3) Reaction of a hemiacetal with an alcohol produces an acetal.
a) All three statements are true.
b) Two of the three statements are true.
c) Only one of the statements is true.
d) None of the statements is true.

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172 Chapter 15: Aldehydes and Ketones Test Bank

15.38 b - FTT Statements:

(1) Aldehydes and ketones readily undergo oxidation to carboxylic acids.
(2) Propanone and dimethyl ketone are two names for the same compound.
(3) The “silver mirror test” distinguishes between aldehydes and ketones.
a) All three statements are true.
b) Two of the three statements are true.
c) Only one of the statements is true.
d) None of the statements is true.

15.39 b - TTF Statements:

(1) Acetals contain three oxygen atoms and hemiacetals contain two oxygen
atoms.
(2) Reduction of an aldehyde, using hydrogen gas, produces a primary alcohol.
(3) In an aldehyde, the carbonyl group can be located on either carbon 1 or
carbon 2.
a) All three statements are true.
b) Two of the three statements are true.
c) Only one of the statements is true.
d) None of the statements is true.

15.40 b - TTF Statements:

(1) In a “dial” two aldehyde groups are present.
(2) Formaldehyde readily participates in polymer formation.
(3) Primary alcohol oxidation is a method for producing ketones.
a) All three statements are true.
b) Two of the three statements are true.
c) Only one of the statements is true.
d) None of the statements is true.

15.41 b - TFT Statements:

(1) Butanal and 2-butanone are constitutional isomers.
(2) The linear notation for an aldehyde is RCOH and that for a ketone is RCOR.
(3) Water molecules can hydrogen bond with aldehyde and ketone molecules.
a) All three statements are true.
b) Two of the three statements are true.
c) Only one of the statements is true.
d) None of the statements is true.

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Test Bank Chapter 15: Aldehydes and Ketones 173

15.42 d - FFF Statements:

(1) The compound 4-oxopentanal contains both an aldehyde and an ether
functional group.
(2) An alkoxy group and a hydroxy group attached to the same carbon atom are
present in both hemiacetals and acetals.
(3) Cyclic aldehyde structures are possible but cyclic ketone structures are not
possible.
a) All three statements are true.
b) Two of the three statements are true.
c) Only one of the statements is true.
d) None of the statements is true.

15.43 c - FFT Statements:

(1) Butanal and butanone are both correct IUPAC names.
(2) The two alcohol molecules produced when an acetal molecule undergoes
hydrolysis are always identical.
(3) Aldehydes and ketones are both classified as carbonyl-containing compounds.
a) All three statements are true.
b) Two of the three statements are true.
c) Only one of the statements is true.
d) None of the statements is true.

15.44 a - TTT Statements:

(1) In the IUPAC nomenclature system, an aldehyde group has priority over a
ketone group.
(2) Addition of an alcohol molecule across the carbon-oxygen double bond of an
aldehyde produces a compound in which the carbonyl carbon atom bears
both an alkoxy group and a hydroxy group.
(3) 2-Propenal contains two fewer hydrogen atoms than propionaldehyde.
a) All three statements are true.
b) Two of the three statements are true.
c) Only one of the statements is true.
d) None of the statements is true.

15.45 b - TFT Statements:

(1) The lachrymator in wood smoke is formaldehyde.
(2) The skin pigment melanin is a polymeric substance containing many
interconnected aldehyde units.
(3) Benedict’s test can be used to detect glucose in urine (diabetes) because
glucose contains an aldehyde group.
a) All three statements are true.
b) Two of the three statements are true.
c) Only one of the statements is true.
d) None of the statements is true.

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174 Chapter 15: Aldehydes and Ketones Test Bank

MATCHING QUESTIONS

Characterize each compound on the left in terms of functional groups present using the response list
on the right. Responses on the right may be used more than once or need not be used at all.
15.46 a Pentanal
a) one aldehyde functional group
15.47 c 3-Pentanone b) two aldehyde functional groups
c) one ketone functional group
15.48 b Pentanedial d) one aldehyde and one ketone functional
group
15.49 c 3-Methylpentanone

15.50 d 3-Oxopentanal

For each pair of compounds on the left, select a correct characterization from the response list on the
right. Responses on the right may be used more than once or need not be used at all.

15.51 a Acetone a) have the same molecular formula but are

Propanal different compounds

15.52 c Heptanal
Benzaldehyde but have different molecular formulas

15.53 a Diethylketone
Pentanal

15.54 d Acetaldehyde
Ethanal

15.55 c 2,2-Dimethylbutanal
Cyclohexanone

For each of the compound characterizations on the left, select from the response list on the right the
number of constitutional isomers that exist. Responses on the right may be used more than once or
need not be used at all.

15.56 a Saturated four-carbon aldehyde

15.57 d Saturated four-carbon monochloroaldehyde

15.58 b Methylcyclohexanone

15.59 b Saturated noncyclic five-carbon ketone

15.60 b Molecular formula of C4H8O

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Test Bank Chapter 15: Aldehydes and Ketones 175

For each set of reactants on the left, select a correct product characterization from the response list on
the right. Responses on the right may be used more than once or need not be used at all.

15.61 a Aldehyde
Alcohol
Acid catalyst

15.62 b Ketone
Two alcohols
Acid catalyst

15.63 b Hemiacetal
Alcohol
Acid catalyst

15.64 d Aldehyde
Hydrogen
Ni catalyst

15.65 d Ketone
Hydrogen
Ni catalyst

For each of the reaction types on the left, select from the response list on the right the type of organic
compound produced. Responses on the right may be used more than once or need not be used at all.

O
15.66 a Oxidation of R C H
O
15.67 d Oxidation of R C R d) no reaction occurs
OH
15.68 b Oxidation of R CH R
O
15.69 c Reduction of R C R
O
15.70 c Reduction of R C H

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