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Sample Questions

 

Organic Chemistry, 7e (Bruice)

Chapter 4   Isomers: The Arrangement of Atoms in Space

 

1) What type of isomers are CH3CH2OCH3 and CH3CH2CH2OH?

1.    A) constitutional

2.    B) symmetrical

3.    C) configurational

4.    D) conformational

5.    E) stereochemical

Answer:  A

Section:  4-1

 

2) What is the relationship between the following compounds?

 

 

1.    A) configurational isomers

2.    B) conformational isomers

3.    C) constitutional isomers

4.    D) structural isomers

5.    E) positional isomers

Answer:  A

Section:  4-1

 

3) What is the relationship between the following compounds?

 

1.    A) constitutional isomers

2.    B) enantiomers

3.    C) diastereomers

4.    D) conformational isomers

5.    E) superimposable without bond rotation

Answer:  A

Section:  4-1

 

4) What is the relationship between the structures shown below?

 

1.    A) not isomers

2.    B) constitutional isomers

3.    C) conformational isomers

4.    D) configurational isomers

5.    E) enantiomers

Answer:  B

Section:  4-1

 

5) What is the relationship between the structures shown below?

 

1.    A) diastereomers

2.    B) constitutional isomers

3.    C) conformational isomers

4.    D) configurational isomers

5.    E) enantiomers

Answer:  B

Section:  4-1

 

6) Identify the pair of compounds.

 

 

 

1.    A) identical

2.    B) conformation isomers

3.    C) constitutional isomers

4.    D) configurational isomers

5.    E) none of the above

Answer:  D

Section:  4-1

 

7) Which of the following cannot exhibit chirality?

1.    A) 2, 3-dibromobutane

2.    B) 1, 3-dibromobutane

3.    C) 1, 2-dichlorobutane

4.    D) 1, 4-dibromobutane

5.    E) 1-bromo-2-chlorobutane

Answer:  D

Section:  4-2

 

8) Which of the following compounds is chiral?

1.    A)

2.    B)

3.    C)

4.    D)

5.    E)

Answer:  B

Section:  4-2

 

9) Is the molecule shown below chiral or achiral?

 

Answer:  achiral

Section:  4-2

 

10) Is the molecule shown below chiral or achiral?

 

Answer:  chiral

Section:  4-2

 

11) Is the molecule shown below chiral or achiral?

 

Answer:  achiral

Section:  4-2

 

12) Is the molecule shown below chiral or achiral?

 

Answer:  achiral

Section:  4-2

 

 

13) Identify the compounds that are not chiral.

 

Answer:  A, B, and D

Section:  4-2

14) Which of the following compounds has an asymmetric center?

 

1.    A) I

2.    B) II

3.    C) III

4.    D) IV

5.    E) V

Answer:  C

Section:  4-3

 

15) How many asymmetric centers are present in a molecule of 2,4,6-trimethylheptane?

1.    A) 0

2.    B) 1

3.    C) 2

4.    D) 3

5.    E) 4

Answer:  A

Section:  4-3

 

16) How many asymmetric centers are present in the compound shown below?

 

1.    A) 1

2.    B) 2

3.    C) 3

4.    D) 4

5.    E) 5

Answer:  C

Section:  4-3

 

17) How many asymmetric centers are present in the compound below?

 

Answer:  5

Section:  4-3

 

18) Identify the pair of compounds.

 

 

 

1.    A) identical

2.    B) conformational isomers

3.    C) constitutional isomers

4.    D) configurational isomers

5.    E) none of the above

Answer:  D

Section:  4-3

19) Give the number of asymmetric centers in limonene.

 

 

 

1.    A) 2

2.    B) 3

3.    C) 1

4.    D) 5

5.    E) 4

Answer:  C

Section:  4-3

 

20) Identify the compound(s) with asymmetric centers.

1.    A)

2.    B)

3.    C)

4.    D)

5.    E)

Answer:  C

Section:  4-3

 

21) A and B are stereoisomers. They are nonsuperimposable and are mirror images of one another. Which of the following best describes the relationship between A and B?

1.    A) structural isomers

2.    B) enantiomers

3.    C) conformational isomers

4.    D) diastereomers

5.    E) constitutional isomers

Answer:  B

Section:  4-4

 

22) What is the relationship between the structures shown below?

 

1.    A) enantiomers

2.    B) diastereomers

3.    C) configurational isomers

4.    D) identical compounds

5.    E) constitutional isomers

Answer:  D

Section:  4-4

 

23) Which of the following compounds is an enantiomer of the structure below?

 

1.    A)

2.    B)

3.    C)

4.    D) A and B

5.    E) It does not have an enantiomer.

Answer:  E

Section:  4-4

 

24) Which of the following statements correctly describes the molecule shown below?

 

1.    A) It is achiral.

2.    B) It is meso.

3.    C) Its asymmetric center possesses the R

4.    D) The mirror image of this molecule is its enantiomer.

5.    E) The molecule possesses enantiotopic hydrogens.

Answer:  D

Section:  4-4

 

25) Choose the enantiomer of the compound below.

 

 

1.    A)

2.    B)

3.    C)

4.    D)

5.    E)

Answer:  E

Section:  4-4

 

26) Which of the following terms best describes the pair of compounds shown:  enantiomers, diastereomers, or the same compound?

 

Answer:  the same compound

Section:  4-4

 

27) The compound CH3CHClCH2CH=CHCH2CH3 contains only one asymmetric center. Explain why it has four stereoisomers.

Answer:  In addition to the single asymmetric center which may be either R or S, it also contains a carbon-carbon double bond which may be either E or Z. Thus, the four stereoisomers can be designated E, R; E, S; Z, R; and Z, S.

Section:  4-5

 

28) Draw the enantiomer of the compound below.

 

Answer:

Section:  4-6

 

29) Identify the following compounds as R or S.

 

 

 

1.    A) S, S, R

2.    B) S, R, S

3.    C) R, S, S

4.    D) S, S, S

5.    E) R, R, R

Answer:  D

Section:  4-6

 

30) Identify all pairs of enantiomers.

 

 

1.    A) B and D, A and C

2.    B) A and C

3.    C) B and D

4.    D) A and B, A and D, B and C, C and D

5.    E) B and D, A and B, A and D, B and C, C and D

Answer:  C

Section:  4-6

 

31) Identify all identical compounds.

 

 

1.    A) B and D, A and C

2.    B) A and C

3.    C) B and D

4.    D) A and B, A and D, B and C, C and D

5.    E) B and D, A and B, A and D, B and C, C and D

Answer:  B

Section:  4-6

 

32) Which of the following compounds has an S configuration?

1.    A)

2.    B)

3.    C)

4.    D)

5.    E)

Answer:  B

Section:  4-7

 

33) Which of the following compounds has an R configuration?

1.    A)

2.    B)

3.    C)

4.    D)

5.    E)

Answer:  A

Section:  4-7

34) Which of the following groups has the highest priority using the Cahn, Ingold, Prelog rules?

1.    A)

2.    B)

3.    C) —OH

4.    D) —O—CH3

5.    E)

Answer:  D

Section:  4-7

 

35) The configuration of R-(+)-glyceraldehyde is as follows:

What is the absolute configuration of (-)-lactic acid?

1.    A) R configuration

2.    B) L configuration

3.    C) S configuration

4.    D) R and S configuration

5.    E) D and L configuration

Answer:  A

Section:  4-7

36) Indicate whether each of the following structures has the R or S configuration. What is the relationship between the two structures?

 

 

Answer:

 

 

Therefore, the two compounds are enantiomers.

Section:  4-7

 

37) Label each asymmetric center in the compound below as R or S.

 

Answer:

Section:  4-7

 

38) Draw the structure of (S)-1-bromo-1-chloropropane. Take particular care to indicate three-dimensional stereochemistry detail properly.

Answer:

Section:  4-7

39) Provide the structure of (R)-4-octanol.  Be careful to indicate proper stereochemistry.

Answer:

Section:  4-7

 

40) Identify the following compounds as R or S.

 

 

 

1.    A) R, S, R

2.    B) S, R, R

3.    C) S, S, S

4.    D) R, R, R

5.    E) S, S, R

Answer:  A

Section:  4-7

 

 

41) Provide a careful structure for (2R,3S)-2,3-dibromohexane.

Answer:

Section:  4-7

 

42) Provide a careful structure for (2S,3S)-2,3-dibromohexane.

Answer:

Section:  4-7

43) Provide a careful structure for (2S,3R)-2,3-dibromohexane.

Answer:

Section:  4-7

 

44) Label each asymmetric center as R or S.

Answer:

 

Section:  4-7

 

45) Provide a careful structure for (2R,3S,4S)-2-bromo-4-methyl-3-hexanol.

 

Answer:

 

Section:  4-7

46) Provide a careful structure for (2S,3R,4R)-2-bromo-4-methyl-3-hexanol.

Answer:

Section:  4-7

 

47) Which of the following is a true statement?

1.    A) All chiral molecules possess a plane of symmetry.

2.    B) All achiral molecules are meso.

3.    C) All molecules which possess a single chirality center of the S configuration are levorotatory.

4.    D) A mixture of achiral compounds will be optically inactive.

5.    E) All molecules which possess two or more chirality centers will be chiral.

Answer:  D

Section:  4-8

 

48) Which of the following is not true of enantiomers?

1.    A) They have the same melting point.

2.    B) They have the same boiling point.

3.    C) They have the same chemical reactivity with non-chiral reagents.

4.    D) They have the same density.

5.    E) They have the same specific rotation.

Answer:  E

Section:  4-9

 

 

49) Which of the following is/are optically inactive?

1.    A) a 50-50 mixture of R and S enantiomers

2.    B) a meso compound

3.    C) every achiral compound

4.    D) a racemic mixture

5.    E) all the above

Answer:  E

Section:  4-9

 

50) Which of the following statements correctly pertains to a pair of enantiomers?

1.    A) They rotate the plane of polarized light by exactly the same amount and in opposite directions.

2.    B) They rotate the plane of polarized light by differing amounts and in opposite directions.

3.    C) They rotate the plane of polarized light by differing amounts and in the same direction.

4.    D) They have different melting points.

5.    E) They have the same melting point, but they have different boiling points.

Answer:  A

Section:  4-9

51) If (S)-glyceraldehyde has a specific rotation of -8.7°, what is the specific rotation of (R)-glyceraldehyde?

8.    A) -8.7°

9.    B) +8.7°

10.  C) 0.0°

11.  D) cannot be determined from the information given

Answer:  B

Section:  4-9

 

52) A mixture of equal amounts of two enantiomers ________.

1.    A) is called a racemic mixture

2.    B) is optically inactive

3.    C) implies that the enantiomers are meso forms

4.    D) both A and B

5.    E) none of the above

Answer:  D

Section:  4-9

 

53) A solution containing 0.96 g of 2-bromooctane in 10 mL ether solution gave an observed rotation of -1.8° in a 10 cm cell at  Calculate the specific rotation of this solution.

Answer:  [α] =

 

[α] =  = -18.75° in ether

Section:  4-9

 

54) A newly isolated natural product was shown to be optically active. If a solution of 2.0 g in 10 mL of ethanol in a 50 cm tube gives a rotation of +2.57°, what is the specific rotation of this natural product?

Answer:  +2.57°

Section:  4-9

 

55) Twenty grams of a compound was dissolved in 100 mL of solvent and gave an observed rotation of -20 degrees.  The sample tube is 4 dm long.  Calculate the specific rotation.

Answer:  -25°

Section:  4-9

 

56) The specific rotation of a pure substance is 1.68°. What is the specific rotation of a mixture containing 75% of this isomer and 25% of the (-) isomer?

1.    A) +1.68°

2.    B) 0°

3.    C) +1.26°

4.    D) +0.84°

5.    E) +.042°

Answer:  D

Section:  4-10

57) The specific rotation of a pure substance is -5.90°. What is the percentage of this isomer in a mixture with an observed specific rotation of -2.95°?

1.    A) 25%

2.    B) 50%

3.    C) 75%

4.    D) 80%

5.    E) 0%

Answer:  C

Section:  4-10

 

58) (-)-Mandelic acid has a specific rotation of -158°. What would be the specific rotation of a solution which contains 40% (-)-mandelic acid and 60% (+)-mandelic acid?

1.    A) +95°

2.    B) +63°

3.    C) +32°

4.    D) -32°

5.    E) -63°

Answer:  C

Section:  4-10

 

59) The specific rotation of (R)-(+)-glyceraldehyde is +8.7°.  If a mixture of glyceraldehydes enantiomers is 80% S and 20% R, what is the specific rotation of the mixture?

Answer:  -5.2°

Section:  4-10

 

 

60) A sample of (+) and (-)-3-chlorohexane has a rotation of -20 degrees.  Pure (+) -3-chlorohexane has a rotation of +40 degrees.  Calculate the enantiomeric excess and the amount of (-) and (+)-3-chlorohexane in the original sample.

Answer:  50%, 75% (-), 25% (+)

Section:  4-10

 

61) What is the relationship between the following compounds?

 

1.    A) superimposable without bond rotation

2.    B) constitutional isomers

3.    C) conformational isomers

4.    D) diastereomers

5.    E) enantiomers

Answer:  E

Section:  4-11

62) What is the relationship between the structures shown below?

 

1.    A) enantiomers

2.    B) diastereomers

3.    C) configurational isomers

4.    D) identical compounds

5.    E) constitutional isomers

Answer:  B

Section:  4-11

 

 

63) What is the relationship between the following compounds?

 

1.    A) enantiomers

2.    B) diastereomers

3.    C) constitutional isomers

4.    D) conformational isomers

5.    E) identical compounds

Answer:  A

Section:  4-11

 

64) What is the relationship between the following compounds?

 

1.    A) enantiomers

2.    B) diastereomers

3.    C) constitutional isomers

4.    D) conformational isomers

5.    E) identical compounds

Answer:  B

Section:  4-11

65) Which of the following is chiral?

1.    A) cis-1-bromo-3-chlorocyclobutane

2.    B) trans-1-bromo-3-chlorocyclobutane

3.    C) cis-1,4-dimethylcyclohexane

4.    D) cis-1,3-dimethylcyclohexane

5.    E) trans-1,3-dimethylcyclohexane

Answer:  E

Section:  4-11

 

 

66) How many diastereomers exist for the compound below?

 

1.    A) 2

2.    B) 4

3.    C) 6

4.    D) 7

5.    E) 8

Answer:  C

Section:  4-11

 

67) Which of the following terms best describes the pair of compounds shown:  enantiomers, diastereomers, or the same compound?

 

Answer:  enantiomers

Section:  4-11

68) Which of the following terms best describes the pair of compounds shown:  enantiomers, diastereomers, or the same compound?

 

Answer:  diastereomers

Section:  4-11

 

 

69) Which of the following terms best describes the pair of compounds shown:  enantiomers, diastereomers, or the same compound?

 

Answer:  diastereomers

Section:  4-11

 

70) Draw the structure of (2R,3S)-dichloropentane. Take particular care to indicate three-dimensional stereochemistry detail properly.

Answer:

Section:  4-11

 

71) Draw the structure of (2S,3R)-dichloropentane. Take particular care to indicate three-dimensional stereochemistry detail properly.

Answer:

Section:  4-11

72) Draw the structure of any diastereomer of (2R,3S)-dichloropentane. Take particular care to indicate three-dimensional stereochemistry detail properly.

Answer:

Section:  4-11

 

73) Steroisomers which are not mirror image isomers are ________.

Answer:  diastereomers

Section:  4-11

 

 

74) Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound?

 

Answer:  the same compound

Section:  4-11

 

75) Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound?

 

Answer:  the same compound

Section:  4-11

 

76) Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound?

 

Answer:  enantiomers

Section:  4-11

77) Draw the stereoisomers of 1,3-dichlorocyclopentane.

Answer:

Section:  4-11

 

 

78) Provide a perspective drawing of (2R,3S)-1,2,3-trichloropentane.

Answer:

Section:  4-11

 

79) Provide a perspective drawing of the enantiomer of (2R,3S)-1,2,3-trichloropentane.

Answer:

Section:  4-11

 

80) Provide a perspective drawing of each diastereomer of (2R,3S)-1,2,3-trichloropentane.

Answer:

Section:  4-11

81) Identify all pairs of diastereomers.

 

 

1.    A) B and D, A and C

2.    B) A and C

3.    C) B and D

4.    D) A and B, A and D, B and C, C and D

5.    E) B and D, A and B, A and D, B and C, C and D

Answer:  D

Section:  4-11

 

 

82) Identify all meso compounds.

 

 

1.    A) B and D, A and C

2.    B) A and C

3.    C) B and D

4.    D) A and B, A and D, B and C, C and D

5.    E) B and D, A and B, A and D, B and C, C and D

Answer:  B

Section:  4-11

83) Identify all configurational isomers.

 

 

1.    A) B and D, A and C

2.    B) A and C

3.    C) B and D

4.    D) A and B, A and D, B and C, C and D

5.    E) B and D, A and B, A and D, B and C, C and D

Answer:  E

Section:  4-11

 

84) Which of the following is a meso compound?

1.    A)

2.    B)

3.    C)

4.    D)

5.    E)

Answer:  A

Section:  4-13

 

85) What is the relationship between the following compounds?

 

1.    A) enantiomers

2.    B) diastereomers

3.    C) constitutional isomers

4.    D) conformational isomers

5.    E) identical compounds

Answer:  E

Section:  4-13

 

86) Which of the following is a meso compound?

1.    A) trans-1, 4-dimethylcyclohexane

2.    B) cis-1, 3-dimethylcyclohexane

3.    C) trans-1, 3-dimethylcyclohexane

4.    D) cis-1, 4-dimethylcyclohexane

5.    E) trans-1, 2-dimethylcyclohexane

Answer:  B

Section:  4-13

 

87) How many stereoisomers exist with the following basic connectivity?

 

BrCH2CH(CH3)CH2CH3

1.    A) 0

2.    B) 1

3.    C) 2

4.    D) 4

5.    E) 8

Answer:  C

Section:  4-13

 

88) How many stereoisomers exist with the following basic connectivity?

 

CH3CHClCH2CHClCH3

1.    A) 0

2.    B) 1

3.    C) 2

4.    D) 3

5.    E) 4

Answer:  D

Section:  4-13

89) Which of the statements below correctly describes an achiral molecule?

1.    A) The molecule has a nonsuperimposable mirror image.

2.    B) The molecule exhibits optical activity when it interacts with plane-polarized light.

3.    C) The molecule has an enantiomer.

4.    D) The molecule might be a meso form.

5.    E) none of the above

Answer:  D

Section:  4-13

 

90) Consider the molecules with molecular formula C2H2Br2Cl2.

1.    a) Draw a structure that is optically inactive because it does not have an asymmetric center.

2.    b) Draw a structure that is optically inactive because it is a meso compound.

3.    c) Draw a structure that is optically active because it is chiral.

Answer:

1.    a)

no chirality center

b)

meso compound

c)

chiral

Section:  4-13

 

 

91) Draw the structure of a meso form of 1,3-dichlorocyclopentane. Take particular care to indicate three-dimensional stereochemistry detail properly.

Answer:

Section:  4-13

92) Label the molecule shown as chiral or achiral.

 

Answer:  Achiral

Section:  4-13

 

93) Label the molecule shown as chiral or achiral.

 

Answer:  Chiral

Section:  4-13

 

94) Label the molecule shown as chiral or achiral.

 

Answer:  Achiral

Section:  4-13

 

 

95) Label the molecule shown as chiral or achiral.

 

Answer:  Chiral

Section:  4-13

96) Is the molecule shown chiral? Is it a meso compound?

 

Answer:  not chiral; not meso

 

Section:  4-13

 

97) Is the molecule shown chiral? Is it a meso compound?