Chapter 5

Exam
Name___________________________________
MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.
1) W hat type of isomers are CH3 CH2 OCH3 and CH3 CH2 CH2 OH?
1)
A) symmetrical
B) constitutional
C) conformational
D) configurational
E) stereochemical
Answ er: B
Se ction: 5-1
2) W hat is the relationship betw een the follow ing compounds?
2)
A) positional isomers
B) configurational isomers
C) constitutional isomers
D) conformational isomers
E) structural isomers
Answ er: B
Se ction: 5-1
A) enantiomers
B) diastereomers
C) conformational isomers
D) superimposable w ithout bond r otation
E) constitutional isomers
Answ er: E
Se ction: 5-1
3)
4) W hat is the relationship betw een the structures show n below ?
4)
A) not isomers
B) enantiomers
D) configurational isomers
E) conformational isomers
Answ er: C
Se ction: 5-1
5)
A) conformational isomers
C) enantiomers
D) constitutional isomers
E) diastereomers
Answ er: D
Se ction: 5-1
6) W hich of the follow ing compounds is never chiral?
6)
A) 1, 3-dibromobutane
B) 1-bromo-2-chlorobutane
C) 1, 4-dibromobutane
D) 2, 3-dibromobutane
E) 1, 2-dichlorobutane
Answ er: C
Se ction: 5-2
7) W hich of the follow ing compounds is chiral?
7)
A)
B)
C)
D)
E)
Answ er: C
Se ction: 5-2
SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.
8)
8) Is the molecule show n below chiral or achiral?
Answ er: achiral

Se ction: 5-2
9)
Answ er: chiral

Se ction: 5-2
10)
Answ er: achiral

Se ction: 5-2
11)
Answ er: achiral

Se ction: 5-2
12) W hich of the follow ing compounds has an asymmetric center?
A) I
B) II
C) III
12)
D) IV
E) V
Answ er: C
Se ction: 5-3
13) How many asymmetric centers are present in a molecule of 2,4,6 -trimethylheptane?
A) 0
B) 1
C) 2
D) 3
13)
E) 4
Answ er: A
Se ction: 5-3
14) How many asymmetric centers are present in the compound show n below ?
A) 1
B) 2
C) 3
D) 4
Answ er: C
Se ction: 5-3
14)
E) 5
15) How many asymmetric centers are present in the compound below ?
15)
Answ er: 5
Se ction: 5-3
16) A and B are stereoisomers. They are nonsuperimposable and are mirror images of one another.
16)
W hich of the follow ing best describes the relationship betw een A and B?
A) diastereomers
B) structural isomers
C) enantiomers
Answ er: C
Se ction: 5-4
A) configurational isomers
B) enantiomers
C) diastereomers
E) identical compounds
Answ er: E
Se ction: 5-4
17)
18) W hich of the follow ing compounds is an enantiomer of the structure below ?
18)
A)
B)
C)
D) A and B
E) It does not have an enantiomer.
Answ er: E
Se ction: 5-4
19) W hich of the follow ing statements cor rectly describes the molecule show n below ?
A) It is achiral.
B) The mirror image of this molecule is its enantiomer.
C) It is meso.
D) It's asymmetric center possesses the R configuration.
E) The molecule possesses enantiotopic hydrogens.
Answ er: B
Se ction: 5-4
19)
20) Choose the enantiomer of the compound b elow .
20)
A)
B)
C)
D)
E)
Answ er: D
Se ction: 5-4
21) W hich of the follow ing terms best describes the pair of compounds show n:
enantiomers, diastereomers, or the same compound?
Answ er: the same compound

Se ction: 5-4
21)
22) The compound CH3 CHClCH2 CH=CHCH2 CH3 contains only one asymmetric center.
22)
Explain w hy it has four stereoisomers.

Answ er: In addition to the single asymmetric center w hich may be either R or S, it also
contains a carbon-carbon double bond w hich may be either E or Z. Thus, the
four stereoisomers can be designated E, R; E, S; Z, R; and Z, S.
Se ction: 5-5
23) Draw the enantiomer of the compound below .
23)
Answ er:
Se ction: 5-6
24) W hich of the follow ing compounds has an S configuration?
A)
B)
C)
D)
E)
Answ er: C
Se ction: 5-7
10
24)
25) W hich of the follow ing compounds has an R configuration?

A)
B)
C)
D)
E)
Answ er: B
Se ction: 5-7
11
25)
26) W hich of the follow ing groups has the highest prior ity using the Cahn, Ingold, Prelog r ules?
26)
A)
B)
C)
CH3
D)
OH
E)
Answ er: C
Se ction: 5-7
27) The configur ation of R-(+)-glyceraldehyde is as follow s:
W hat is the absolute configuration of (-)-lactic acid?
A) L configur ation
B) S configur ation
C) R configur ation
D) R and S configur ation
E) D and L configur ation
Answ er: C
Se ction: 5-7
12
27)
28) Indicate w hether each of the follow ing structures has the R or S configuration. W hat is
28)
the relationship betw een the tw o structures?
assign prior ities to each group.

Answ er:
Therefor e, the tw o compounds are enantiomers.

Se ction: 5-7
29) Label each asymmetric center in the compound below as R or S.
29)
Answ er:
Se ction: 5-7
30) Draw the structure of (S)-1-bromo-1-chloropropane. Take particular care to indicate

three-dimensional stereochemistry detail properly.
Answ er:
Se ction: 5-7
13
30)
31) Provide the structure of (R)-4-octanol. Be careful to indicate proper stereochemistry.
31)
Answ er:
Se ction: 5-7
32) W hich of the follow ing is a true statement?
32)
A) A mixture of achiral compounds w ill be optically inactive.

B) All chiral molecules possess a plane of symmetry.
C) All achiral molecules are meso.
D) All molecules w hich possess a single chirality center of the S configuration are
levorotatory.
E) All molecules w hich possess 2 or more chirality centers w ill be chiral.
Answ er: A
Se ction: 5-8
33) W hich of the follow ing is not true of enantiomers?
33)
A) They have the same specific rotation.

B) They have the same boiling point.
C) They have the same chemical reactivity w ith non -chiral reagents.
D) They have the same density.
E) They have the same melting point.
Answ er: A
Se ction: 5-9
34) W hich of the follow ing is/are optically inactive?
34)
A) every achiral compound

B) a racemic mixture
C) a meso compound
D) a 50-50 mixture of R and S enantiomers
E) all the above
Answ er: E
Se ction: 5-9
35) W hich of the follow ing statements cor rectly pertains to a pair of enantiomers?
A) They rotate the plane of polarized light by differing amounts and in the same direction.
B) They have the same melting point, but they have different boiling points.
C) They rotate the plane of polarized light by differing amounts and in opposite directions.
D) They rotate the plane of polarized light by exactly the same amount and in opposite
directions.
E) They have different melting points.
Answ er: D
Se ction: 5-9
14
35)
36) If (S)-glyceraldehyde has a specific rotation of -8.7, w hat is the specific rotation of
36)
(R)-glyceraldehyde?
A) 0.0
B) -8.7
C) +8.7
D) cannot be determined from the information given
Answ er: C
Se ction: 5-9
37) A mixture of equal amounts of tw o enantiomers __________.
37)
A) is called a r acemic mixture

B) is optically inactive
C) implies that the enantiomers are meso forms
D) both A and B
E) none of the above
Answ er: D
Se ction: 5-9
38) A solution containing 0.96 g of 2-bromooctane in 10 mL ether solution gave an
38)
observed rotation of -1.8 in a 10 cm cell at 20 C. Calculate the specific rotation of this

solution.
Answ er:
T
D
1c
20 C
D
1.8
1 dm
0.96 g
= -18.75 in ether
10 mL
Se ction: 5-9
39) A new ly isolated natural product w as show n to b e optically active. If a solution of 2.0 g
39)
in 10 mL of ethanol in a 50 cm tube gives a rotation of +2.57, w hat is the specific

rotation of this natural product?
Answ er: +2.57

Se ction: 5-9
40) The specific rotation of a pure substance is 1.68. W hat is the specific rotation of a mixture
40)
containing 75% of this isomer and 25% of the (-) isomer?

A) +1.68
B) +0.84
C) +1.26
D) +.042
E) 0
Answ er: B
Se ction: 5-10
41) The specific rotation of a pure substance is -5.90. W hat is the percentage of this isomer in a
mixture w ith an ob served specific rotation of -2.95?
A) 50%
B) 75%
C) 0%
D) 80%
Answ er: B
Se ction: 5-10
15
E) 25%
41)
42) (-)-Mandelic acid has a specific rotation of -158. W hat w ould be the specific rotation of a
42)
solution w hich contains 40% (-)-mandelic acid and 60% (+)-mandelic acid?
A) +32
B) -32
C) +63
D) +95
E) -63
Answ er: A
Se ction: 5-10
43) The specific rotation of (R)-(+)-glyceraldehyde is +8.7. If a mixture of glyceraldehydes
43)
enantiomers is 80% S and 20% R, w hat is the specific rotation of the mixture?
Answ er: -5.2
Se ction: 5-10
44)
A) constitutional isomers
B) enantiomers
C) superimposable w ithout bond r otation
E) diastereomers
Answ er: B
Se ction: 5-11
A) diastereomers
D) identical compounds
E) enantiomers
Answ er: A
Se ction: 5-11
16
45)
46)
A) enantiomers
B) conformational isomers
D) diastereomers
E) identical compounds
Answ er: A
Se ction: 5-11
47)
A) diastereomers
B) identical compounds
E) enantiomers
Answ er: A
Se ction: 5-11
48) W hich of the follow ing is chiral?
48)
A) cis-1-bromo-3-chlorocyclobutane
B) cis-1,4-dimethylcyclohexane
C) trans-1,3-dimethylcyclohexane
D) trans-1-bromo-3-chlorocyclobutane
E) cis-1,3-dimethylcyclohexane
Answ er: C
Se ction: 5-11
17
49) How many diastereomers exist for the compound below ?
A) 7
B) 2
C) 8
49)
D) 4
E) 6
Answ er: E
Se ction: 5-11
50)
Answ er: enantiomers

Se ction: 5-11
Answ er: diastereomers

Se ction: 5-11
18
51)
52)

Se ction: 5-11
53) Draw the structure of (2R,3S)-dichloropentane. Take particular care to indicate
53)

Answ er:
Se ction: 5-11
54) Draw the structure of (2S,3R)-dichloropentane. Take particular care to indicate
54)

Answ er:
Se ction: 5-11
55) Draw the structure of any diastereomer of (2R,3S)-dichloropentane. Take particular
55)
care to indicate three-dimensional stereochemistry detail properly.

Answ er:
Se ction: 5-11
56) Steroisomers w hich are not mirror image isomers are __________.
Se ction: 5-11
19
56)
57)

Se ction: 5-11
58)

Se ction: 5-11
59)
Answ er: enantiomers

Se ction: 5-11
60) Draw the stereoisomers of 1, 3-dichlorocyclopentane.

Answ er:
Se ction: 5-11
20
60)
61) Provide a perspective draw ing of (2R,3S)-1,2,3-trichloropentane.
61)
Answ er:
Se ction: 5-11
62) Provide a perspective draw ing of the enantiomer of (2R,3S)-1,2,3-trichloropentane.
62)
Answ er:
Se ction: 5-11
63) Provide a perspective draw ing of each diastereomer of (2R,3S)-1,2,3-trichloropentane.
63)
Answ er:
Se ction: 5-11
64) W hich of the follow ing is a meso compound?
64)
A)
B)
21
C)
D)
E)
Answ er: D
Se ction: 5-12
A) enantiomers
B) identical compounds
D) diastereomers
Answ er: B
Se ction: 5-12
22
65)
66) W hich of the follow ing is a meso compound?
66)
A) cis-1, 3-dimethylcyclohexane
B) trans-1, 2-dimethylcyclohexane
C) cis-1, 4-dimethylcyclohexane
D) trans-1, 3-dimethylcyclohexane
E) trans-1, 4-dimethylcyclohexane
Answ er: A
Se ction: 5-12
67) How many stereoisomers exist w ith the follow ing basic connectivity?
67)
BrCH2 CH(CH3 )CH2 CH3

A) 0
B) 1
C) 2
D) 4
E) 8
Answ er: C
Se ction: 5-12
68) How many stereoisomers exist w ith the follow ing basic connectivity?
68)
CH3 CHClCH2 CHClCH3

A) 0
B) 1
C) 2
D) 3
E) 4
Answ er: D
Se ction: 5-12
69) W hich of the statements below cor rectly describes an achiral molecule?
A) The molecule might be a meso form.
B) The molecule has a nonsuperimposable mirror image.
C) The molecule exhibits optical activity w hen it interacts w ith plane-polarized light.
D) The molecule has an enantiomer.
E) none of the above
Answ er: A
Se ction: 5-12
23
69)
70) Consider the molecules w ith molecular formula C2 H2 Br 2 Cl2 .
a)
70)
Draw a structure that is optically inactive because it does not have an asymmetric
center.
b)
Draw a structure that is optically inactive because it is a meso compound.
c)
Draw a structure that is optically active because it is chiral.
Answ er: a)
no chirality center
b)
meso compound
c)
chiral
Se ction: 5-12
71) Draw the structure of a meso form of 1, 3-dichlor ocyclopentane. Take particular care to
indicate three-dimensional stereochemistry detail properly.
Answ er:
Se ction: 5-12
24
71)
72) Lab el the molecule show n as chiral or achiral.
72)
Answ er: Achiral

Se ction: 5-12
73)
Answ er: Chiral

Se ction: 5-12
74)
Answ er: Achiral

Se ction: 5-12
75)
Answ er: Chiral

Se ction: 5-12
25
76) W hat is the configuration of the follow ing compound?
76)
A) 3R, 3S
B) 2R, 3R
C) 2S, 3R
D) 2S, 3S
E) Can't do R and S; the compound is achiral.
Answ er: D
Se ction: 5-13
77) In the Fischer proj ection below , w hat are the configurations of the tw o asymmetric centers?
A) 2R, 3R
B) 2S, 3R
C) 2S, 3S
D) 2R, 3S
E) cannot be determined from structure
Answ er: A
Se ction: 5-13
26
77)
78) Label each asymmetrical carbon in the compound below as R or S.
78)
Answ er:
Se ction: 5-13
79) Draw a perspective for mula of (2R,3S)-3-bromo-2-butanol.
79)
Answ er:
Se ction: 5-13
80) Draw any diastereomer of (2R,3R)-2,3-dichlor opentane. Be careful to indicate proper

stereochemistry.
Answ er:
Se ction: 5-13
27
80)
81) Can one predict w hether a compound w ith a single asymmetric center is dextro- or
81)
levorotatory based on the R/S assignment at this asymmetric center? Explain briefly.
Answ er: No. R/S assignment is purely a convention of nomenclature and is completely
independent of the direction in w hich plane-polarized light is rotated by the
compound.
Se ction: 5-13
82) Assign an R or S configurational label to each asymmetric center in the molecule below .
82)
Answ er:
Se ction: 5-13
83) Briefly describe how tw o enantiomers might be separated.
83)
Answ er: The tw o compounds can be converted to diastereomers, separated based on

different physical properties of these diastereomers, and subsequently returned
to their original forms or chromatographic separation using a chiral stationary
phase.
Se ction: 5-16
84) The compound below contains an asymmetric center at nitrogen. W hy can't individual
stereoisomers of this compound be isolated at room temperature?
Answ er: Nitrogen has a pair of nonbonding electrons that allow it to turn "inside out" at
room temperature. Because of r apid inversion, the individual stereoisomers
cannot be isolated.
Se ction: 5-17
28
84)
85) W hat configurations are found in the product(s) of the reaction below ?
85)
A) 1S,2S only
B) 1R,2S only
C) 1R,2R only
D) an equal mixture of 1R,2R and 1S,2S
E) an equal mixture of 1R,2R and 1R,2S
Answ er: D
Se ction: 5-19
86) Provide the structure of the maj or or ganic product of each of the follow ing reactions.
Answ er:
Se ction: 5-19
29
86)

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Exam

2) W hat is the relationship betw een the follow ing compounds?

3) W hat is the relationship betw een the follow ing compounds?

4) W hat is the relationship betw een the structures show n below ?

5) W hat is the relationship betw een the structures show n below ?

6) W hich of the follow ing compounds is never chiral?

7) W hich of the follow ing compounds is chiral?

8) Is the molecule show n below chiral or achiral?

Answ er: achiral

9) Is the molecule show n below chiral or achiral?

Answ er: chiral

10) Is the molecule show n below chiral or achiral?

Answ er: achiral

11) Is the molecule show n below chiral or achiral?

Answ er: achiral

20) Choose the enantiomer of the compound b elow .

Answ er: the same compound

Explain w hy it has four stereoisomers.

23) Draw the enantiomer of the compound below .

25) W hich of the follow ing compounds has an R configuration?

27) The configur ation of R-(+)-glyceraldehyde is as follow s:

W hat is the absolute configuration of (-)-lactic acid?

the relationship betw een the tw o structures?

assign prior ities to each group.

Therefor e, the tw o compounds are enantiomers.

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

30) Draw the structure of (S)-1-bromo-1-chloropropane. Take particular care to indicate

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

A) A mixture of achiral compounds w ill be optically inactive.

33) W hich of the follow ing is not true of enantiomers?

A) They have the same specific rotation.

34) W hich of the follow ing is/are optically inactive?

A) every achiral compound

37) A mixture of equal amounts of tw o enantiomers __________.

A) is called a r acemic mixture

observed rotation of -1.8 in a 10 cm cell at 20 C. Calculate the specific rotation of this

in 10 mL of ethanol in a 50 cm tube gives a rotation of +2.57, w hat is the specific

Answ er: +2.57

containing 75% of this isomer and 25% of the (-) isomer?

48) W hich of the follow ing is chiral?

49) How many diastereomers exist for the compound below ?

enantiomers, diastereomers, or the same compound?

Answ er: enantiomers

Answ er: diastereomers

enantiomers, diastereomers, or the same compound?

Answ er: diastereomers

53) Draw the structure of (2R,3S)-dichloropentane. Take particular care to indicate

three-dimensional stereochemistry detail properly.

54) Draw the structure of (2S,3R)-dichloropentane. Take particular care to indicate

three-dimensional stereochemistry detail properly.

55) Draw the structure of any diastereomer of (2R,3S)-dichloropentane. Take particular

care to indicate three-dimensional stereochemistry detail properly.

enantiomers, diastereomers, or the same compound?

Answ er: the same compound

enantiomers, diastereomers, or the same compound?

Answ er: the same compound

enantiomers, diastereomers, or the same compound?

Answ er: enantiomers

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

61) Provide a perspective draw ing of (2R,3S)-1,2,3-trichloropentane.

62) Provide a perspective draw ing of the enantiomer of (2R,3S)-1,2,3-trichloropentane.

63) Provide a perspective draw ing of each diastereomer of (2R,3S)-1,2,3-trichloropentane.

66) W hich of the follow ing is a meso compound?