Chapter 05 - Stereochemistry At Tetrahedral Centers

Solution Manual for Organic Chemistry 9th Edition McMurry

1305080483 9781305080485
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mcmurry-1305080483-9781305080485/
Exhibit 5-1
For the following question(s) MATCH each definition to a term from the list below. Place the letter of the term in the
blank to the left of the definition.
a. racemates f. meso compounds
b. chirality center g. optically active
c. chirality h. prochirality center
d. diastereomers i. optically inactive
e. enantiomers j. achiral
1. ____ are organic molecules which rotate the plane of polarization of plane-polarized light.
ANSWER: g
POINTS: 1

2. _____ is the reason for "handedness" in molecules; the property of an object that causes it to be nonsuperimposable on
its mirror image.
ANSWER: c
POINTS: 1

3. _____ are stereoisomers that are not mirror images.

ANSWER: d
POINTS: 1

4. _____ is an atom in a molecule that is bonded to four different atoms or groups of atoms.
ANSWER: b
POINTS: 1

5. _____ are molecules which contain a plane of symmetry and chirality centers, but are achiral.
ANSWER: f
POINTS: 1

6. _____ is an sp3-hybridized atom that can become a chirality center by changing one of its attached groups.
ANSWER: h
POINTS: 1

7. The specific rotation of a compound is denoted by the symbol:

a. R
b. S
c. α

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Chapter 05 - Stereochemistry At Tetrahedral Centers

d.
ANSWER: d
POINTS: 1

Exhibit 5-2
Place asterisks at all the chirality centers in each molecule below.

8.

ANSWER:

POINTS: 1

9.

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Chapter 05 - Stereochemistry At Tetrahedral Centers
ANSWER:

POINTS: 1

10.

ANSWER:

POINTS: 1

11.

ANSWER:

POINTS: 1

12.

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Chapter 05 - Stereochemistry At Tetrahedral Centers
ANSWER:

POINTS: 1

13.

ANSWER:

POINTS: 1

Exhibit 5-3
Assign R, S configurations to each indicated chirality center in the molecules below.

14. Refer to Exhibit 5-3. The configuration of this carbon atom (A) is _____.
ANSWER: R
POINTS: 1

15. Refer to Exhibit 5-3. The configuration of this carbon atom (B) is _____.
ANSWER: S
POINTS: 1

16. Refer to Exhibit 5-3. The configuration of this carbon atom (C) is _____.
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Chapter 05 - Stereochemistry At Tetrahedral Centers
ANSWER: R
POINTS: 1

17. Refer to Exhibit 5-3. The configuration of this carbon atom (D) is _____.
ANSWER: S
POINTS: 1

18. Refer to Exhibit 5-3. The configuration of this carbon atom (E) is _____.
ANSWER: S
POINTS: 1

Exhibit 5-4
Consider the structure of streptimidone to answer the following question(s).

19. Refer to Exhibit 5-4. Assign R or S configuration to each chirality center indicated in streptimidone.
ANSWER:

POINTS: 1

20. Refer to Exhibit 5-4. Based on the number of chirality centers, how many stereoisomers of streptimidone are possible?
ANSWER: Streptimidone has two chirality centers so there are 22, or 4, possible stereoisomers.
POINTS: 1

21. Refer to Exhibit 5-4. Will streptimidone have a meso stereoisomer? Explain your answer.
ANSWER: No. Meso compounds are compounds that contain chirality centers, but possess a plane of symmetry. Because
the substituents on the chiral carbons are different in streptimidone it is impossible for any stereoisomer to
have a plane of symmetry.
POINTS: 1

Exhibit 5-5
Label each pair of stereoisomers below as:
a. enantiomers
b. diastereomers
c. identical
Place the letter of the correct answer in the blank to the left of the pair of stereoisomers.

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Chapter 05 - Stereochemistry At Tetrahedral Centers

22. _____

ANSWER: a
POINTS: 1

23. _____

ANSWER: c
POINTS: 1

24. _____

ANSWER: b
POINTS: 1

25. _____

ANSWER: b
POINTS: 1

26. _____

ANSWER: c
POINTS: 1

27. _____

ANSWER: a
POINTS: 1

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Chapter 05 - Stereochemistry At Tetrahedral Centers

28. _____

ANSWER: b
POINTS: 1

29. Draw a wedge-dash projection of (2R,3S)-dibromobutane.

ANSWER:

POINTS: 1

30. Draw a Newman projection of the most stable conformation of (2R,3S)-dibromobutane sighting down the C2−C3
bond.
ANSWER:

POINTS: 1

31. (2R,3S)-Dibromobutane is:

a. optically active.
b. racemic.
c. dextrorotatory.
d. a meso compound.
ANSWER: d
POINTS: 1

32. Estriol, a potent estrogenic hormone, has been isolated from the urine of pregnant women. When 40 mg of estriol is
dissolved in 1.0 mL of dioxane and placed in a sample tube with 1 dm path length a rotation of +2.32° is observed.
Calculate the specific rotation for estriol.
ANSWER:

POINTS: 1

Exhibit 5-6
Refer to the structure below to answer the following question(s).

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Chapter 05 - Stereochemistry At Tetrahedral Centers

33. Refer to Exhibit 5-6. (S)-(−)-Serine:

a. is dextrorotatory
b. rotates plane-polarized light in a counterclockwise direction
c. rotates plane-polarized light in a clockwise direction
d. is racemic
ANSWER: b
POINTS: 1

34. Refer to Exhibit 5-6. Draw the enantiomer of (S)-(−)-serine in a wedge-dash projection.
ANSWER:

POINTS: 1

35. Refer to Exhibit 5-6. Give the complete name of the enantiomer of (S)-(−)-serine.
ANSWER: (R)-(+)-serine
POINTS: 1

Exhibit 5-7
A natural product having [α]D = +40.3° has been isolated and purified.

36. Refer to Exhibit 5-7. This information indicates that the natural product:
a. is racemic.
b. does not rotate plane-polarized light.
c. is levorotatory.
d. is dextrorotatory.
ANSWER: d
POINTS: 1

37. Refer to Exhibit 5-7. Two structures have been proposed for this natural product. Circle the structure that is consistent
with the information presented and briefly explain your choice.

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Chapter 05 - Stereochemistry At Tetrahedral Centers
ANSWER:

The information presented indicates that the natural product is optically active. To be optically active
molecules must be chiral—that is, they must not have a plane of symmetry. The cyclic structure, although has
chirality centers, has a plane of symmetry, indicated by the dashed line on the structure, and can, therefore, not
be optically active. The circled structure has four chirality centers, and is not symmetric. We would expect it
to be optically active.
POINTS: 1

Exhibit 5-8
Identify the indicated hydrogens in the following molecules as pro-R or pro-S.

38.

ANSWER:

POINTS: 1

39.

ANSWER:

POINTS: 1

Exhibit 5-9
Identify the indicated faces in the following molecules as re or si.

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Chapter 05 - Stereochemistry At Tetrahedral Centers

40.

ANSWER:

POINTS: 1

41.

ANSWER:

POINTS: 1

42. Acetoacetate synthase catalyzes the addition of pyruvate to β-ketobutyrate to yield α-aceto-α-hydroxybutyrate. If the
addition occurs from the si face of β-ketobutyrate, what is the stereochemistry of the product?

ANSWER: Addition of the aceto group to the si face results in the S enantiomer of α-aceto-α-hydroxybutyrate.

POINTS: 1

43. Explain why a work glove is chiral but disposable surgical gloves are not.

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Chapter 05 - Stereochemistry At Tetrahedral Centers
ANSWER: Surgical gloves are not made to wear on a left hand or right hand but can be worn on either hand with an
equally good fit. This type of glove is symmetrical with respect to the positioning of the covering that goes on
the thumb - it has a plane of symmetry.
or
Work gloves have "front" and "back" sides. The thumb is positioned differently with respect to the digits.
Surgical gloves have five symmetrical digits. They do not have "front" and "back" sides.
POINTS: 1

44. A white solid known to be enantiomerically pure is dissolved in water. This solution produced an observed optical
rotation of +45.6°. The solution was allowed to stand and the optical rotation was measured repeatedly producing the data
shown in the table.

Observed Rotation
Time (min)
(°)
10 +39.9
20 +5.6
30 -1.2
40 -23.4
40 -23.4
Explain the pattern of observed rotation.
ANSWER: Some type of reaction, possibly a hydrolysis, is occurring and the optically active dextrorotatory compound is
being converted to the levorotatory enantiomer.
The change may be due to the production of a new compound with a specific rotation of -23.4°. This might be
verified by using this value to identify the compound if enough other information is known.
Assuming an equilibrium is established, an alternate explanation could be that it appears from the final value
of the observed rotation that an equilibrium mixture of the two forms and that the levorotatory from
predominates in the mixture.

POINTS: 1

45. Draw a structure for a singly substituted chiral chloroalkane that contains four carbon atoms. Indicate the chirality
center with an asterisk (*).
ANSWER:

The chirality center is indicated by the asterisk (*),

POINTS: 1

46. Which of the following objects is not chiral?

a. baseball glove
b. ballerina slipper
c. corkscrew
d. comb
e. All are chiral.
ANSWER: d
POINTS: 1

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Chapter 05 - Stereochemistry At Tetrahedral Centers
47. Which of the following would be has the highest priority according to the sequence rules?
a. —SH b. —NH2
c. —CH3 d. —OH
ANSWER: a
POINTS: 1

48. Which of the following arranges the groups in order of decreasing priority according to the sequence rules?
a. CH3 > CH2CH3 > CH2OH > CO2H b. CH3 > CH2CH3 > CO2H >CH2OH
c. CH2OH > CO2H > CH2CH3 > CH3 d. CO2H > CH2OH > CH2CH3 > CH3
ANSWER: d
POINTS: 1

49. In which of the following groups can the carbon atom be a chiral center?
a.
b.
c.
d.
e. The carbon atoms cannot be a chiral center in any of these groups.
ANSWER: e
POINTS: 1

50. Which of the following compounds will rotate the plane of polarized light?
a. b.

c. d.

ANSWER: c
POINTS: 1

51. For which of the following generic substances is it not possible to isolate the enantiomers? (R1, R2 and R3 represent
different groups.)
a.

b.

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Chapter 05 - Stereochemistry At Tetrahedral Centers
c.

d. It is possible to isolate the enantiomers of all of these.

e. It is not possible to isolate the enantiomers of any of these.
ANSWER: a
POINTS: 1

52. In muscles during strenuous exercise, under anaerobic conditions lactic acid builds up due to the following reaction.

The carbon atom indicated by the asterisk is

a. chiral b. achiral
c. prochiral d. both achiral and prochiral
ANSWER: d
POINTS: 1

53. A compound with specific rotation, [α]D = +35.4° reacts to form a single product. The product of the reaction shows
no optical activity. This could mean that the product:
a. is a racemate.
b. does not have any chiral centers.
c. is a meso compound.
d. Any of the above are possible explanations.
ANSWER: d
POINTS: 1

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