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Chapter 16

front 1

1) Which type of compound does not contain a carbonyl group?

A) ketone

B) aldehyde

C) amine

D) ester

E) carboxylic acid

back 1

C

front 2

2) Which functional group contains a carbonyl group and a hydroxyl group bonded to the same carbon atom?

A) ester

B) amide

C) ketone

D) aldehyde

E) carboxylic acid

back 2

E

front 3

3) Which functional group contains a carbonyl group and an ether linkage bonded to the same carbon atom?

A) amide

B) ketone

C) carboxylic acid

D) ester

E) aldehyde

back 3

D

front 4

4) One of the major differences between aldehydes and ketones as compared to other carbonyl compounds is that in aldehydes and ketones

A) the carbonyl carbon has bond angles of 120°C, unlike the comparable bond angles in other carbonyl compounds. B) the polar carbon-oxygen bond is less reactive than the hydrocarbon portion of the molecule.

C) the molar masses tend to be much smaller than in the other types of compounds.

D) the carbonyl group carbon atom is bonded to atoms that do not attract electrons strongly.

E) none of the above

back 4

D

front 5

5) The carbonyl group is

A) found only in aldehydes and ketones.

B) produced by reduction reactions of primary or secondary alcohols.

C) a functional group in which carbon and oxygen are joined by a double bond.

D) a general term for any functional group involving a carbon-oxygen bond.

E) a functional group with a 6-membered ring where at least one atom is oxygen

back 5

C

front 6

6) All of the statements concerning the carbonyl group in aldehydes and ketones are true except

A) The bond is polar, with a slight negative charge on the oxygen atom.

B) The bond angles about the central carbon atom are 120°.

C) Because the bond is polar, carbonyl groups readily form hydrogen bonds with each other.

D) In condensed form the carbonyl group can be written as -CHO.

E) The carbonyl group is planar.

back 6

C

front 7

7) Which molecule is formaldehyde?

back 7

A

front 8

8) Which molecule is 2-butanone?

back 8

C

front 9

9) Which molecule is propanal?

back 9

E

front 10

10) Which molecule is acetone?

back 10

D

front 11

11) Which is the correct systematic name for the molecule shown?

A) ethyl methyl acetone

B) methyl propyl ketone

C) 4-hexanone

D) propyl methyl ketone

E) 3-hexanone

back 11

E

front 12

12) Which molecule is a ketone?

back 12

A

front 13

13) Which molecule is an aldehyde?

back 13

D

front 14

14) The IUPAC name for acetone is

A) 2-propanone.

B) dimethyl ketone.

C) 1-propanone.

D) 3-propanal.

E) 2-propanal.

back 14

A

front 15

15) The IUPAC name for dimethyl ketone is

A) 3-propanal.

B) 2-propanone.

C) acetone.

D) 1-propanone.

E) 2-propanal.

back 15

B

front 16

16) The correct name for CH3-CH(CH3)-CH2-CHO is

A) 3-methyl-1-butanone.

B) 2-methylbutanal.

C) 3-methylbutanal.

D) isopentanal.

E) 3-methyl-1-butanal.

back 16

C

front 17

17) The correct name for

CH3-CH(CH3)-CH2-CO-CH3 is

A) isobutyl acetone.

B) 2-methyl-4-butanone.

C) 4-methyl-2-butanone.

D) 4-methyl-2-pentanone.

E) 2-methyl-4-pentanone.

back 17

D

front 18

18) What is the IUPAC name of the compound shown?

A) 4-heptanone

B) 2-methyl-3-hexanone

C) 3-heptanone

D) isopropyl n-propyl ketone

E) 4-methyl-5-hexanone

back 18

B

front 19

19) What is the IUPAC name of the compound shown?

A) isopentanal

B) 2-methyl-4-butanone

C) 2-methyl-1-butanone

D) 2-methylbutanal

E) 3-methylbutanal

back 19

E

front 20

20) Which of the following names does not fit a real compound?

A) 3-octanone

B) 2-butanone

C) 3-methyl-3-pentanone

D) all are correct

E) 3-methyl-1-pentanone

back 20

E

front 21

21) Which of the following names does not fit a real compound?

A) 3-ethylpentanal

B) 4-methylpentanal

C) all are correct

D) ethanal

E) 3-methyl-2-pentanal

back 21

E

front 22

22) Which of the following is not a property of aldehydes and ketones?

A) They cannot form hydrogen bonds with water because they have no hydrogen atoms bonded to oxygen.

B) Most have distinctive odors.

C) They have higher boiling points than alkanes of similar molar mass.

D) They are polar.

E) They have lower boiling points than alcohols of similar molar mass.

back 22

A

front 23

23) All of the following are properties of acetone except

A) flammable.

B) intoxicating.

C) solvent for organic substances.

D) volatile.

E) nutrient

back 23

E

front 24

24) Which of the following is a use of formaldehyde?

A) flavoring

B) preservative

C) hormone

D) solvent

E) sweetener

back 24

B

front 25

25) Which compound has the lowest boiling point?

A) CH3-CO-CH3

B) CH3-CHO

C) CH3-CH2-OH

D) CH3-CH2-CH2-OH

E) CH3-CH2-CHO

back 25

B

front 26

26) Which compound has the highest boiling point?
A) CH3-CHO
B) CH3-CH2-CHO
C) CH3-CH2-OH
D) CH3-CO-CH3
E) CH3-CH2-CH2-OH

back 26

E

front 27

27) Which compound has the lowest boiling point?

A) CH3-CH2-CHO

B) CH3-CH2-CH3

C) CH3-CH2-CH2-OH

D) CH3-CH2-CH2-CH3

E) CH3-CH2-OH

back 27

B

front 28

29) All of the following are true concerning a two-carbon aldehyde except

back 28

A

front 29

30) All of the following are true concerning a three-carbon ketone except

back 29

B

front 30

31) The common name of an industrial solvent used in many manufacturing processes is methyl ethyl ketone. The correct systematic name and structural formula of this compound are

back 30

A

front 31

32) Tollens' reagent is used to

A) distinguish amines from aldehydes.

B) distinguish aldehydes from ketones.

C) reduce aldehydes.

D) reduce ketones.

E) oxidize ketones.

back 31

B

front 32

33) Oxidation of an aldehyde produces a

A) primary alcohol.

B) secondary alcohol.

C) carboxylic acid.

D) ketone.

E) tertiary alcohol.

back 32

C

front 33

34) Oxidation of a ketone produces

A) an aldehyde

B) a carboxylic acid

C) a primary alcohol

D) a secondary alcohol

E) no reaction

back 33

E

front 34

35) All of the following statements about oxidation of carbonyls are true except

A) Oxidation of ketones produces esters.

B) Tollen's test involves reduction of Ag+.

C) Oxidation of aldehydes produces carboxylic acids.

D) Benedict's test involves reduction of Cu2+.

E) none of the above

back 34

A

front 35

36) All of the following statements about oxidation of carbonyls are true except

A) The Benedict's test involves reduction of Cu2+.

B) Ketones do not react with mild oxidizing agents.

C) The Tollens' test involves oxidation of Ag+.

D) Oxidation of aldehydes produces carboxylic acids.

E) All of the statements are true.

back 35

C

front 36

37) Which compound will give a positive Tollen's test?

A) pentanal

B) 3-pentanone

C) 2-pentanone

D) pentanoic acid

E) pentane

back 36

A

front 37

38) Which observation denotes a positive Tollen's test?

A) A silver wire dissolves.

B) A brick-red precipitate forms.

C) The light blue color of the reagent disappears.

D) A silver deposit forms on the glass surface.

E) Bubbles of oxygen gas are produced.

back 37

D

front 38

39) Which observation denotes a positive Benedict's test?

A) A mirror-like deposit forms from a colorless solution.

B) A red precipitate forms from a blue solution.

C) A red-brown solution becomes clear and colorless.

D) A pale yellow solution with an odor of chlorine changes to a purple color.

E) A purple solution yields a brown precipitate.

back 38

B

front 39

40) What is the product of oxidation of butanal?

A) butane

B) 2-butanol

C) 1-butanol

D) butanoic acid

E) no reaction

back 39

D

front 40

41) What is the product of oxidation of 2-butanone?

A) butanoic acid

B) butanal

C) 2-butanol

D) 1-butanol

E) no reaction

back 40

E

front 41

42) Which compound will give a positive Tollen's test?

back 41

B

front 42

43) What is product of the oxidation of a ketone?

A) an aldehyde

B) a hemiacetal

C) a carboxylic acid

D) an alcohol

E) none, ketones don't oxidize.

back 42

E

front 43

44) What is the element that causes oxidation in the Tollens test for aldehydes?

A) gold

B) copper

C) lead

D) silver

E) platinum

back 43

D

front 44

45) Reduction of an aldehyde produces a

A) tertiary alcohol.

B) carboxylic acid.

C) secondary alcohol.

D) ketone.

E) primary alcohol.

back 44

E

front 45

46) Reduction of a ketone produces a(an)

A) carboxylic acid.

B) secondary alcohol.

C) aldehyde.

D) tertiary alcohol.

E) primary alcohol.

back 45

B

front 46

47) What is the product of reduction of butanal?

A) butanoic acid

B) butane

C) 2-butanol

D) 1-butanol

E) no reaction

back 46

D

front 47

48) What is the product of reduction of 2-butanone?

A) butanal

B) 1-butanol

C) 2-butanol

D) butanoic acid

E) no reaction

back 47

C

front 48

49) What is the product of the reduction of 3-methyl-2-pentanone?

A) 3-methyl-2-pentanal

B) 2-methyl-3-pentanol

C) 3-methyl-2-pentanol

D) 3-methyl-2-pentene

E) no reaction

back 48

C

front 49

50) In biochemical reactions, reduction of carbonyl groups is carried out by

A) H2.

B) lactic acid.

C) NADH.

D) pyruvic acid.

E) NaBH4

back 49

C

front 50

51) Reduction of aldehydes and ketones is a

A) one-step reaction involving the H- ion.

B) one-step reaction involving the H+ ion.

C) two-step reaction involving the H- and OH- ions.

D) two-step reaction involving the H- and H+ ions.

E) two-step reaction involving the OH- and H+ ions.

back 50

D

front 51

52) What reaction conditions are needed to cause formation of an acetal from the same reactants that form hemiacetals?

A) high temperature

B) limited amount of alcohol as reactant

C) metallic catalyst

D) excess aldehyde or ketone as reactant

E) acid catalyst

back 51

E

front 52

53) The reverse reaction of acetal formation is

A) oxidation.

B) combustion.

C) hydrolysis.

D) reduction.

E) esterification.

back 52

C

front 53

54) Which pair of compounds can react to form a hemiacetal?

A) CH3CH2CHO and CH3CH2OH

B) CH3CH2CHO and CH3COOH

C) CH3COCH3 and CH3COOH

D) CH3COCH3 and CH3CH2CHO

E) CH3COOH and CH3CH2OH

back 53

A

front 54

55) A compound with an -OH group and an ether-like -OR group bonded to the same carbon atom is

A) an acetal.

B) a hemiacetal.

C) a simple ether.

D) an aldol.

E) a diol

back 54

B

front 55

56) A compound with two ether-like - OR groups bonded to the same carbon atom is

A) an aldol.

B) a hemiacetal.

C) a simple ether.

D) an acetal.

E) a diol

back 55

D

front 56

57) Hydrolysis of an acetal will produce

A) one aldehyde or ketone + two ethers.

B) one aldehyde or ketone + two alcohols.

C) one aldehyde or ketone + two waters.

D) two aldehydes or ketones + one alcohol.

E) two aldehydes or ketones + one ether.

back 56

B

front 57

58) Since hemiacetals are unstable, they are seldom found in significant quantities in reaction mixtures. An exception to this statement is the formation of hemiacetals

A) in an acid-catalyzed reaction.

B) in a base-catalyzed reaction.

C) from aldehyde and alcohol groups within the same molecule.

D) from carbonyl compounds and alcohols with different R groups.

E) from carbonyl compounds and alcohols with identical R groups.

back 57

C

front 58

59) To what class of compounds does glucose belong?

A) cyclic ketone

B) cyclic aldehyde

C) cyclic acetal

D) cyclic hemiacetal

E) cyclic acid

back 58

D

front 59

59) Which of the following is a hemiacetal?

back 59

B

front 60

60) Which of the following is an acetal?

back 60

C

front 61

61) What is the major organic product of the following reaction?

back 61

B

front 62

62) The result of a hydrolysis reaction is what?

A) getting the chemicals wet

B) having an oxidation reduction reaction result in hydration of the molecule

C) splitting of a molecule into the component substances

D) one that forms water upon reaction

E) addition of water across a double bond

back 62

C

front 63

63) Which of the following products is formed when hydrogen is reacted with 3-methyl-2-butanone?

A) a primary alcohol

B) a secondary alcohol

C) a tertiary alcohol

D) an acetal

back 63

B