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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.
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.
15.10 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
15.12 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.
15.15 a The oxidizing agent in the Tollens test for the presence of an aldehyde is
a) Ag+
b) Ag
c) Cu2+
d) Cu2O
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.
15.19 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.
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).
15.22 d Which of the following is a correct notation for the aldehyde functional group?
a) CHO
O
b) C H
O
c) C
15.23 a Which of the following aldehydes is paired with an incorrect IUPAC name?
Cl O
a) CH3 CH CH2 C H ;2chloro4butanal
Cl O
b) CH3 CH2 CH C H ;2chlorobutanal
Cl Cl O
c) CH3 CH CH C H ;2,3dichlorobutanal
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
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
15.28 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
b) CH3 CH CH3
OH
CH3
c) CH3 C OH
CH3
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
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
OH O
a) CH3 CH CH2 C H
O O
b) CH3 C CH2 C H
OH O
c) CH3 CH CH2 C CH3
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.
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.
15.52 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.
15.58 b Methylcyclohexanone
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