Chapter.16 Aldehydes and Ketones Exam Prep 4th Edition

General, Organic and Biological Chemistry, 4e (Smith)

Chapter 16 Aldehydes and Ketones

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

A) RCOOH

B) RCHO

C) RCOR

D) RCOH

E) RCH2OH

2) What is the condensed formula of the compound shown below?

A) CH3CO(CH2)3CH(CH3)2

B) CH3OC(CH2)3CHCH3CH3

C) CH3CO(CH2)3CHCH3CH3

D) CH3OCCH2CH2CH2CH2CH(CH3)2

3) The compound shown below belongs to what class of compounds?

A) Alkane

B) Aldehyde

C) Ketone

D) Acetal

E) Carboxylic acid

4) The compound shown below belongs to what class of compounds?

A) Alkane

B) Aldehyde

C) Ketone

D) Acetal

E) Carboxylic acid

5) What is the common name of the compound shown below?

A) Benzene aldehyde

B) Benzaldehyde

C) Acetaldehyde

D) Phenone

6) 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

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

A)

B)

C)

D)

8) 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

9) What is the IUPAC name of the compound shown below?

A) 1-pentanone

B) Cyclopentanone

C) Phenone

D) Cyclopentone

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

A)

B)

C)

D)

11) What is the structure of 2-ethyl-4-methyloctanal?

A)

B)

C)

D)

12) Which compound has the highest boiling point?

A) CH3(CH2)5CH3

B) CH3(CH2)4CHO

C) CH3(CH2)4CH2OH

D) All of the compounds have the same boiling point.

13) Which compound has the greatest solubility in water?

A) CH3(CH2)5CHO

B) CH3(CH2)4COCH2CH3

C) CH3CH2CHO

D) The compounds all are equally soluble in water.

14) 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 are soluble in both heptane and water.

15) The Tollens reagent is which of the following?

A) K2Cr2O7

B) H2SO4

C) Cl2

D) Ag2O in aqueous NH4OH

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

A) Alcohols

B) Aldehydes

C) Ketones

D) Carboxylic acids

E) Alcohols and aldehydes

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

A)

B)

C)

D) No reaction occurs.

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

A) CH3(CH2)5CHO

B)

C)

D)

19) Which compound is an example of a ketone?

A)

B)

C)

D)

E) None of the structures are ketones.

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

A)

B)

C)

D)

E) More than one of the compounds will give a positive Tollens test result.

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

A)

B)

C)

D)

22) 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

23) What product is formed when the following molecule is treated with H2 and a Pd catalyst?

A)

B)

C)

D)

24) Which reactant would be needed to form the alcohol product CH3CH2CH2OH by a reduction reaction?

A)

B)

C)

D)

25) What product is formed when the following molecule is treated with H2 and a Pd catalyst?

A)

B)

C)

D)

26) Which reactant would be needed to form the alcohol product shown below by a reduction reaction?

A)

B)

C)

D)

27) 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

28) Which reagent can be used to reduce a ketone?

A) K2Cr2O7

B) H2SO4

C) H2 with Pd metal

D) Ag2O in aqueous NH4OH

29) 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

30) 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

31) Which compound is an acetal?

A)

B)

C)

D)

E)

32) Which compound is a hemiacetal?

A)

B)

C)

D)

E)

33) What hemiacetal is formed in the reaction below?

A)

B)

C)

D)

34) What hemiacetal is formed in the reaction below?

A)

B)

C)

D)

35) What hemiacetal is formed when the hydroxyl aldehyde shown below is cyclized?

A)

B)

C)

D)

36) What products are formed when the acetal below is hydrolyzed with water and sulfuric acid?

A)

B)

C) HOCH2CH2CH2CH2CH3  +  2 CH3OH

D)

37) What is the acetal formed in the reaction below, if two equivalents of alcohol are used?

A)

B)

C)

D)

38) What acetal is formed when the compound shown below is treated with two equivalents of ethanol (CH3CH2OH) in the presences of H2SO4?

A)

B)

C)

D)

39) 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

40) 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

41) What type of compound is shown below?

A) An epoxide

B) A cyclic hemiacetal

C) An aldehyde

D) A cyclic acetal

42) What type of compound is shown below?

A) An epoxide

B) A cyclic hemiacetal

C) An aldehyde

D) A cyclic acetal

43) 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

44) 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

45) What is the name of the compound below?

A) 2-ethylbenzenone

B) 2-ethylacetophenone

C) 2-ethylacetobenzone

D) 2-ethylphenone

46) What is the name of the compound below?

A) 3-chlorobenzenal

B) 3-methanalchlorobenzene

C) M-chlorobenzaldehyde

D) P-chloroacetophenone

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

A)

B)

C)

D)

48) What is the structure of 2-bromo-5-hydroxyheptanal?

A)

B)

C)

D)

49) 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

50) What is the name of the compound below?

A) 1-methoxy-3-methylbenzene

B) 4-methoxy-6-methylbenzaldehyde

C) 4-methoxy-2-methylacetophenone

D) 5-methoxy-3-methyltoluene

51) 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.

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.

53) 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.

54) Deoxyribose is a building block of DNA. Which statement concerning the functional groups present in deoxyribose, shown below, is incorrect?

A) It contains an acetal.

B) It contains an alcohol.

C) It contains a hemiacetal.

D) None of these choices are incorrect.

55) 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.

56) In the correct order, what are the three reactions that convert all-trans-retinal into 11-cis-retinal so that the process of vision can continue?

A) Reduction, Oxidation, Isomerization

B) Reduction, Isomerization, Oxidation

C) Oxidation, Isomerization, Reduction

D) Oxidation, Reduction, Isomerization

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

A)

B)

C)

D)

58) Which of the following is the product of the reduction of acetone, shown below?

A)

B)

C)

D)

59) What product results when cinnamaldehyde is oxidized?

A)

B)

C)

D)

60) What product results when cinnamaldehyde is reduced with excess H2 in the presence of a Pd catalyst?

A)

B)

C)

D)

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

A)

B)

C)

D)

62) The reaction below illustrates oxidation by Tollens reagent.

63) The reaction below illustrates oxidation by Tollens' reagent.

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

65) 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.

66) 11-cis-retinal is a ketone in the rod cells of the eye that is critical for vision.

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

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

69) Acetals are ethers.

70) The compound below is an acetal.

71) The carbohydrate glucose exists predominantly as a cyclic hemiacetal.

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

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

74) The structure below contains both an acetal and hemiacetal.

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

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

77) Vanillin, acetone, and formaldehyde are aldehydes.

78) 4,4-Dimethyl-2-hexanone is a ketone of molecular formula C8H16O that has six carbons in its longest chain.

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

80) The reaction below illustrates oxidation of an aldehyde.

81) The reaction below illustrates oxidation of an aldehyde.

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

83) The aldehyde below produces the indicated product upon oxidation with K2Cr2O7.

84) The compound below is soluble in water and in hexane.

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

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

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

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

89) Oxidation of the aldehyde below gives the indicated product.

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

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

92) The alcohol below has a higher boiling point than the ketone shown.

93) In a process similar to the one characterized by glucose, the ketone below forms the indicated hemiacetal product.

94) The simplest ketone has a much higher boiling point than the simplest aldehyde.

95) All compounds that react with the Tollens reagent react with K2Cr2O7, but not all compounds that react with K2Cr2O7 react with the Tollens reagent.

96) The compound 2-methyl-2-pentanol is oxidized to produce 2-methyl-2-pentanone.

97) Since oxygen is more electronegative than carbon, a carbonyl group is polar.

98) Aldehydes and ketones are polar molecules that are capable of hydrogen bonding with each other.

99) Higher molecular weight aldehydes and ketones (those having six carbons or more) are soluble in water, but insoluble in organic solvents.

100) (CH3)2CHCOCH3 has a lower boiling point than HOCH2CH2CH2CH2OH.

101) Aldehydes play an important role in the sun tanning industry as the active ingredient in commercial tanning agents that produce sunless tans.

102) Aldehydes are easily oxidized by atmospheric oxygen.

103) Aldehydes and ketones undergo addition reactions, which break one of the bonds in the carbon–oxygen double bond.

104) The structure below represents acetone, the simplest ketone.

105) Aldehydes and ketones have ________ (higher/lower) boiling points than alcohols, and ________ (higher/lower) boiling points than hydrocarbons of comparable size.

106) _____ is the simplest aldehyde.

107) The simplest aldehyde contains ________ carbon atom(s), and the simplest ketone contains ________ carbon atom(s).

108) Lactose (structure shown) is the principal carbohydrate in milk. Lactose contains ________ acetal(s) and ________ hemiacetal(s).

109) Solanine is a toxin present in the leaves, stems, and green spots on the skin of potatoes. Solanine contains ________ acetal(s).

110) Ketones are reduced to ________.

111) A student incorrectly names a compound as 4-propyl-2,4-dimethyl-2-chloro-1-pentanone. The correct IUPAC name of this compound is ________.

112) The IUPAC name of the compound shown below is ________.

113) When 2-methyl-3-pentanol is oxidized, the compound ________ is produced.

114) Aldehydes are identified by the suffix ________, and the carbon chain is numbered to place the carbonyl group as the ________ (first/last) carbon atom.