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General, Organic & Biological Chemistry, 5e (Timberlake)
Chapter 14 Aldehydes, Ketones, and Chiral Molecules
14.1 Multiple-Choice Questions
1) Which one of the following compounds is an aldehyde?
A)
OH
|
CH3 - CH - CH3
B)
O
CH3 - CH2 - CH
C) CH3 - CH = CH - CH2 - CH3
D) CH3 - CH2 - O - CH2 - CH3
E) CH3 - SH
Answer: B
Objective: 14.1
Global Outcomes: GO2
2) What are the bond angles in a typical carbonyl group?
A) 45°
B) 90°
C) 109.5°
D) 120°
E) 135°
Answer: D
Objective: 14.1
Global Outcomes: GO2
3) How many carbonyl-containing isomers does the formula C3H6O have?
A) two
B) three
C) five
D) seven
E) eight
Answer: A
Objective: 14.1
Global Outcomes: GO2
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4) The compound 2-propanone is also known as
A) acetone.
B) 2-propanone.
C) dimethyl ketone.
D) β-propanone.
E) propylone.
Answer: A
Objective: 14.1
Global Outcomes: GO2
5) The common name for 2-butanone, a readily available solvent, is
A) methyl acetone.
B) methyl ethyl ketone.
C) β-butanone.
D) butyl ketone.
E) butyl ether.
Answer: B
Objective: 14.1
Global Outcomes: GO2
6) Formaldehyde is used industrially to make
A) polymers.
B) insulating materials.
C) carpeting.
D) All of the above.
E) None of the above.
Answer: D
Objective: 14.1
Global Outcomes: GO7
7) Acetone can be produced by the body when a person is
A) exercising.
B) dieting with high protein diets.
C) ill with a flu.
D) recovering from surgery.
E) sleeping.
Answer: B
Objective: 14.1
Global Outcomes: GO7
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8) Which of the following compounds contains a ketone functional group?
A)
CH3
|
CH3 - C - OH
|
CH3
B)
O
CH3 - CH
C) CH3 - CH2 - O - CH2 -CH3
D)
O
CH3 - CH2 - C - CH3
E) CH3 - O - CH
|
CH3
Answer: D
Objective: 14.1
Global Outcomes: GO2
9) What is the IUPAC name for this compound?
O
CH3 - CH
A) methyl aldehyde
B) 1-ethanaldehyde
C) 1-ethanone
D) ethanal
E) methanal
Answer: D
Objective: 14.1
Global Outcomes: GO2
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10) What is the IUPAC name for this compound?
A) methylcyclohexanone
B) 2,5-dimethylcyclohexanone
C) 1,4-dimethyl-2-cyclohexanone
D) cyclohexyl methyl ketone
E) 1,4-dimethyl-3-cyclohexanone
Answer: B
Objective: 14.1
Global Outcomes: GO2
11) What is the name of this compound?
O
CH3 - C - CH - CH3
|
CH3
A) 2-pentanone
B) methyl propyl ketone
C) 3-methyl-2-butanone
D) 2-methyl-3-butanone
E) 2-methyl-3-ketone butane
Answer: C
Objective: 14.1
Global Outcomes: GO2
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12) Three functional groups found in this compound are
A) alcohol, aromatic, and ether.
B) alcohol, aldehyde, and ether.
C) alcohol, ether, and ketone.
D) aldehyde, ether, and carboxylic acid.
E) cycloalkene, alcohol, and carboxylic acid.
Answer: C
Objective: 14.1
Global Outcomes: GO2
13) Which of the following pairs of compounds are isomers?
A) CH3CH2CH2OH
and
CH3OCH3
B)
O
O
CH3CH2 C CH3
C)
and
CH3 C CH2CH3
CH3CH2 OCH2CH3 and
OH
|
CH3 C CH3
|
CH3
D)
CH3CH2CHOH and
|
CH3
E)
CH3CH2OH
Answer: C
OH
|
CH3 C HCH2CH3
O
and
H C CH3
Objective: 14.1
Global Outcomes: GO2
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14) In all aldehydes except formaldehyde, how many hydrogen atoms is the carbonyl group bonded to?
A) one
B) two
C) three
D) four
Answer: A
Objective: 14.1
Global Outcomes: GO4
15) How many hydrogen atoms is the carbonyl group in a ketone bonded to?
A) none
B) one
C) two
D) three
E) four
Answer: A
Objective: 14.1
Global Outcomes: GO4
16) The carbonyl group consists of
A) a carbon-oxygen-hydrogen structure.
B) a carbon-oxygen single bond.
C) a carbon-oxygen double bond.
D) a carbon-oxygen triple bond.
E) a carbon-oxygen-carbon structure.
Answer: C
Objective: 14.1
Global Outcomes: GO2
17) The oxygen atom in a carbonyl group is ________ the carbon atom.
A) more electronegative than
B) less electronegative than
C) identical in electronegativity to
D) more electropositive than
E) more soluble than
Answer: A
Objective: 14.1
Global Outcomes: GO2
18) How many lone pairs of electrons does the oxygen in a carbonyl group have?
A) None, they're all bonded.
B) one
C) two
D) three
E) four
Answer: C
Objective: 14.1
Global Outcomes: GO4
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19) In the IUPAC naming system, a ketone is named by replacing the -e in the corresponding alkane
name with
A) yne.
B) ene.
C) al.
D) one.
E) ol.
Answer: D
Objective: 14.1
Global Outcomes: GO2
20) In the IUPAC naming system, an aldehyde is named by replacing the -e of the name of the
corresponding alkane with
A) yne.
B) ene.
C) al.
D) one.
E) ol.
Answer: C
Objective: 14.1
Global Outcomes: GO2
21) What is the name of this compound?
A) 2-methylbutanone
B) 3-methyl-2-butanone
C) 2-methyl-3-butanone
D) 3-methylbutanone
E) pentanone
Answer: B
Objective: 14.1
Global Outcomes: GO2
22) Formalin is
A) another name for formaldehyde.
B) a plastic.
C) an aqueous solution of formaldehyde.
D) an excellent solvent.
E) a polymer.
Answer: C
Objective: 14.1
Global Outcomes: GO7
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23) Acetone is a ketone commonly used as a
A) preservative.
B) flavoring agent.
C) fuel.
D) solvent.
E) drain cleaner.
Answer: D
Objective: 14.1
Global Outcomes: GO7
24) The flavoring agent found in vanilla is
A) an aldehyde.
B) a ketone.
C) a hydrocarbon.
D) an ester.
E) a thiol.
Answer: A
Objective: 14.1
Global Outcomes: GO7
25) Aldehydes have higher boiling points than alkanes of similar mass because of
A) hydrogen bonding.
B) dipole-dipole interactions.
C) ionic bonding.
D) covalent bonding.
E) oxygen bonding.
Answer: B
Objective: 14.2
Global Outcomes: GO2
26) The increased boiling point of ketones compared to alkanes and ethers of similar mass is due to
A) hydrogen bonding.
B) dipole-dipole interactions.
C) a bent chain structure.
D) resonance.
E) ionic interactions.
Answer: B
Objective: 14.2
Global Outcomes: GO2
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27) Low-molecular-weight ketones are soluble in water. What is the shortest length of the carbon chain
where insolubility becomes important?
A) one
B) two
C) four
D) five
E) eight
Answer: D
Objective: 14.2
Global Outcomes: GO2
28) Which of the following would not be water soluble?
A) acetone
B) propanal
C) 3-heptanone
D) formaldehyde
E) 2-butanone
Answer: C
Objective: 14.2
Global Outcomes: GO2
29) Which of the following ketones is the most soluble in water?
A) O
CH3 C CH3
B)
O
CH3 - CH - C - CH3
|
CH3
C)
O
CH3 - CH2 - C - CH2 - CH2 - CH3
O
D)
CH3 - C - CH2 - CH2 - CH3
E)
O
CH3 - CH2 - C - CH2 - CH3
Answer: A
Objective: 14.3
Global Outcomes: GO2
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30) The reduction of 3-pentanone with hydrogen in the presence of a nickel catalyst will yield
A) pentane.
B) 2-pentene.
C) diethyl alcohol.
D) 3-pentanol.
E) pentanaldehyde.
Answer: D
Objective: 14.3
Global Outcomes: GO2
31) The addition of hydrogen to an organic compound or the loss of oxygen is called
A) reduction.
B) oxidation.
C) dehydration.
D) halogenation.
E) hydration.
Answer: A
Objective: 14.3
Global Outcomes: GO2
32) The hydrogenation of 2-methylpropanal gives the product
A) 1-butanol.
B) 2-methylpropanoic acid.
C) 2-methyl-3-propanol.
D) 2-methyl-1-propanol.
E) 2-methyl-2-propanol.
Answer: D
Objective: 14.3
Global Outcomes: GO2
33) The Tollens' test may be used to distinguish
A) acids from amines.
B) esters from acids.
C) ketones from alcohols.
D) aldehydes from ketones.
E) alcohols from alkenes.
Answer: D
Objective: 14.3
Global Outcomes: GO2
34) Benedict's test requires an aldehyde and an adjacent
A) saturated carbon.
B) ketone.
C) alcohol.
D) phenyl ring.
E) acid.
Answer: C
Objective: 14.3
Global Outcomes: GO2
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35) Aldehydes and ketones may be reduced to
A) acids.
B) alkanes.
C) ethers.
D) alcohols.
E) esters.
Answer: D
Objective: 14.3
Global Outcomes: GO2
36) Which of the compounds would give a positive Tollens' test?
A)
B)
C)
D)
E)
Answer: B
Objective: 14.3
Global Outcomes: GO2
37) An acetal is formed from two molecules of an alcohol and a(n)
A) aldehyde.
B) ether.
C) carboxylic acid.
D) alkyl ether.
E) ester.
Answer: A
Objective: 14.4
Global Outcomes: GO2
38) How many moles of an alcohol are needed to react with 1 mole of an aldehyde to
form a hemiacetal?
A) 1
B) 1.5
C) 2
D) 3
E) 3.5
Answer: A
Objective: 14.4
Global Outcomes: GO4
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39) How do sugars form cyclic hemiacetals?
A) Two molecules of a sugar react with one another.
B) A molecule of sugar reacts with an added alcohol.
C) A molecule of sugar reacts with itself.
D) A molecule of sugar reacts with an added aldehyde.
E) A sugar molecule decomposes.
Answer: C
Objective: 14.4
Global Outcomes: GO2
40) The product of adding two molecules of an alcohol to an aldehyde in the presence of acid is a(n)
A) acetal.
B) ether.
C) hemiacetal.
D) hemiether.
E) hydroxyl group.
Answer: A
Objective: 14.4
Global Outcomes: GO2
12
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41) Which of these compounds is the hemiacetal that forms when ethanol reacts with propanal?
A)
OH
|
CH3 - CH2 C - O - CH2 - CH3
|
H
B)
OH
|
CH3 - C - O - CH2 - CH3
|
H
C)
O - CH2 – CH2
|
CH3 - CH2 - C - O - CH2 - CH3
|
H
D)
O - CH2 - CH3
|
CH3 - C - O - CH3
|
H
E)
O - CH2 - CH2 - CH3
|
CH3 - C - O - CH2 - CH2 - CH3
|
CH2 - CH2 - CH3
Answer: A
Objective: 14.4
Global Outcomes: GO2
13
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42) What is the acetal formed when propanone reacts with two molecules of methanol?
A)
OH
|
CH3 - C - CH3
|
CH3
B)
O - CH3
|
CH3 - C - CH3
|
O - CH3
C)
O - CH3
|
CH3 - CO - CH3
|
O - CH3
D)
CH3 CH3
|
|
CH3 - C - O - C - CH3
|
H
|
H
E)
OH
|
CH3 - C - CH3
|
O - CH3
Answer: B
Objective: 14.4
Global Outcomes: GO2
43) An enantiomer is
A) a stereoisomer that is not a mirror image of another molecule.
B) a stereoisomer that is a mirror image of another molecule.
C) a diastereoisomer.
D) a structural isomer.
E) a cis-trans isomer.
Answer: B
Objective: 14.5
Global Outcomes: GO2
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44) Chirality occurs when stereoisomers have mirror images that are
A) superimposable.
B) the same.
C) not superimposable.
D) not visible to one another.
E) identical.
Answer: C
Objective: 14.5
Global Outcomes: GO2
45) How many different substituents are required on a carbon atom for it to be chiral?
A) one
B) two
C) three
D) four
E) Any number from 1 to 4; chiralty does not depend on substitution.
Answer: D
Objective: 14.5
Global Outcomes: GO4
46) Which molecule below has stereoisomers with different biological effects?
A) carvone
B) nicotine
C) LSD
D) epinephrine
E) All of the above.
Answer: E
Objective: 14.5
Global Outcomes: GO2
47) Chiral drugs consist of only one enantiomer. The benefits of using a pure enantiomer, rather than a
mixture, include
A) higher potency (lower total dose of drug).
B) elimination of side effects.
C) reduced chances of drug interactions.
D) All of the above.
E) None of the above.
Answer: D
Objective: 14.5
Global Outcomes: GO2
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48) Achiral compounds are those which
A) have no "handedness."
B) have different mirror images.
C) are non-superimposable.
D) have the same formula but different structures.
E) are a racemic mixture.
Answer: A
Objective: 14.5
Global Outcomes: GO2
49) Use the structures below to answer:
A) A is chiral and B is achiral
B) A is achiral and B is chiral
C) both A and B are chiral
D) both A and B are achiral
Answer: D
Objective: 14.5
Global Outcomes: GO2
50) Use the structures below to answer:
A) A is chiral and B is achiral
B) A is achiral and B is chiral
C) both A and B are chiral
D) both A and B are achiral
Answer: A
Objective: 14.5
Global Outcomes: GO2
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14.2 True/False Questions
1) All aldehydes have a carbonyl carbon bonded to at least two hydrogens.
Answer: FALSE
Objective: 14.1
Global Outcomes: GO2
2) Many odors from solvents, paint removers, and perfumes are derived from aldehydes or ketones.
Answer: TRUE
Objective: 14.1
Global Outcomes: GO7
3) In a ketone, the carbonyl group is bonded to two other carbon atoms.
Answer: TRUE
Objective: 14.1
Global Outcomes: GO2
4) The carbonyl group consists of a carbon-oxygen single bond, and a second bond to hydrogen.
Answer: FALSE
Objective: 14.1
Global Outcomes: GO2
5) The carbonyl group does not have a dipole.
Answer: FALSE
Objective: 14.1
Global Outcomes: GO2
6) The suffix -one indicates an aldehyde in the IUPAC system of naming.
Answer: FALSE
Objective: 14.1
Global Outcomes: GO2
7) The suffix -al indicates an aldehyde in the IUPAC system of naming.
Answer: TRUE
Objective: 14.1
Global Outcomes: GO2
8) Acetone is a three-carbon aldehyde.
Answer: FALSE
Objective: 14.1
Global Outcomes: GO2
9) Acetone is sometimes produced in pathological conditions such as diabetes.
Answer: TRUE
Objective: 14.1
Global Outcomes: GO7
10) Formaldehyde is used in solution as a germicide and preservative.
Answer: TRUE
Objective: 14.1
Global Outcomes: GO7
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11) Excessive exposure to formaldehyde can irritate the eyes and respiratory tract.
Answer: TRUE
Objective: 14.1
Global Outcomes: GO7
12) A major flavor component of vanilla is an aldehyde.
Answer: TRUE
Objective: 14.1
Global Outcomes: GO2
13) The name of this compound is 3-butanone.
Answer: FALSE
Objective: 14.1
Global Outcomes: GO2
14) The carbonyl group gives aldehydes higher boiling points than alkanes of similar mass.
Answer: TRUE
Objective: 14.2
Global Outcomes: GO2
15) The carbonyl group gives ketones lower boiling points than alkanes of similar mass.
Answer: FALSE
Objective: 14.2
Global Outcomes: GO2
16) Carbonyl compounds having fewer than four carbon atoms are very water soluble.
Answer: TRUE
Objective: 14.2
Global Outcomes: GO2
17) Hexanal would be soluble in water.
Answer: FALSE
Objective: 14.2
Global Outcomes: GO2
18) Propanal is more soluble than pentanal.
Answer: TRUE
Objective: 14.2
Global Outcomes: GO2
19) Acetone would give a positive Tollens' test.
Answer: FALSE
Objective: 14.3
Global Outcomes: GO2
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20) The Tollens' test is used to distinguish between aldehydes and ketones.
Answer: TRUE
Objective: 14.3
Global Outcomes: GO2
21) Primary alcohols are oxidized to ketones.
Answer: FALSE
Objective: 14.3
Global Outcomes: GO2
22) Ketones are reduced to secondary alcohols.
Answer: TRUE
Objective: 14.3
Global Outcomes: GO2
23) Benedict's test can be used to determine whether an α-hydroxyaldehyde functional group is present.
Answer: TRUE
Objective: 14.3
Global Outcomes: GO2
24) An acetal is formed from an aldehyde or ketone and one molecule of alcohol.
Answer: FALSE
Objective: 14.4
Global Outcomes: GO2
25) A hemiacetal has alkoxy and hydroxyl functional groups bonded to the same carbon.
Answer: TRUE
Objective: 14.4
Global Outcomes: GO2
26) Glucose forms a cyclic hemiacetal.
Answer: TRUE
Objective: 14.4
Global Outcomes: GO2
27) This compound is an acetal.
Answer: TRUE
Objective: 14.4
Global Outcomes: GO2
28) Enantiomers are mirror images of each other.
Answer: TRUE
Objective: 14.5
Global Outcomes: GO2
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29) A chiral carbon atom can have fewer than four different groups bonded to it.
Answer: FALSE
Objective: 14.5
Global Outcomes: GO2
30) Enantiomers may have very different tastes or smells.
Answer: TRUE
Objective: 14.5
Global Outcomes: GO2
31) 2-butanol is a chiral molecule.
Answer: TRUE
Objective: 14.5
Global Outcomes: GO2
32) 1-butanol is a chiral molecule.
Answer: FALSE
Objective: 14.5
Global Outcomes: GO2
33) Enantiomers have superimposable mirror images.
Answer: FALSE
Objective: 14.5
Global Outcomes: GO2
34) The biological activity of one of a set of enantiomers may be very different from the biological activity
of the other optical isomers.
Answer: TRUE
Objective: 14.5
Global Outcomes: GO2
35) This compound is chiral.
Answer: TRUE
Objective: 14.5
Global Outcomes: GO2
20
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14.3 Matching Questions
Select the correct name for the following.
A) 3-propanone
B) 1-propanone
C) diethyl ketone
D) propanal
1)
O
CH3CH2 C CH2CH3
Objective: 14.1
Global Outcomes: GO2
2)
O
CH3CH2 C H
Objective: 14.1
Global Outcomes: GO2
Answers: 1) C 2) D
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Match the structural formula with the correct functional group.
A) aldehyde
B) ether
C) ketone
3)
O
CH3CH
Objective: 14.1
Global Outcomes: GO2
4)
O
CH3 C CH2CH3
Objective: 14.1
Global Outcomes: GO2
5) CH3CH2OCH3
Objective: 14.1
Global Outcomes: GO2
6)
O
CH3CH2 C H
Objective: 14.1
Global Outcomes: GO2
Answers: 3) A 4) C 5) B 6) A
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Identify the product, if any, that would form in each of the following reactions.
A) CH3CH3
B) CH3CH2CH3
C) OH
|
CH3 C HCH3
D)
O
CH3 C OH
E) CH3CH2OH
7)
O
CH3 C H
Objective: 14.3
Global Outcomes: GO2
8)
O
CH3 C CH3 + H2
Objective: 14.3
Global Outcomes: GO2
9)
O
CH3 C H + H2
Objective: 14.3
Global Outcomes: GO2
Answers: 7) D 8) C 9) E
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