Stereochemistry Practce PDF
Stereochemistry Practce PDF
Stereochemistry Practce PDF
5
PART I
1) Is the molecule shown below chiral or achiral?
OH
OH
2) Is the molecule shown below chiral or achiral?
H
C
CH3
CO2OH
CH2OH
C
HO2C
CO2H
Cl
5) Is the molecule shown below chiral or achiral?
CH3
CH3
O
6) Which of the following terms best describes the pair of compounds shown: enantiomers,
diastereomers, or the same compound?
CH3
C
H
CO2OH
CO2H
NH2
H2N
H
CH3
7) Which of the following terms best describes the pair of compounds shown: enantiomers,
diastereomers, or the same compound?
CH3
OH
H3C
HO
8) Label each asymmetric carbon in the compound below as R or S.
OH
CH3
9) Label each asymmetric carbon in the compound below as R or S.
OH
H
CH3
CH3
OH
Cl
11) Draw the structure of (2R,3S)-2,3-dichloropentane. Take particular care to indicate threedimensional stereochemical detail properly.
12) Draw the structure of (S)-1-bromo-1-chloropropane. Take particular care to indicate threedimensional stereochemical detail properly.
13) Draw the structure of a meso form of 1,3-dichlorocyclopentane. Take particular care to
indicate three-dimensional stereochemical detail properly.
14) How many asymmetric carbons are present in the compound below?
CH3
15) How many asymmetric carbons are present in the compound below?
HOH2C
O
HO
HO
OH
OH
16) How many asymmetric carbons are present in the compound below?
CO2H
H
OH
OH
CO2H
17) How many asymmetric carbons are present in the compound below?
-ethyl-2,2,4-trimethylpentane
18) Can the molecule shown below be properly described as a meso compound?
19) Can the molecule shown below be properly described as a meso compound?
Cl
Cl
20) Can the molecule shown below be properly described as a meso compound?
Cl
Cl
21) Draw the structure of (1R, 2R)-1-bromo-2-chlorocyclobutane. Take particular care to indicate
stereochemistry properly.
22) Stereoisomers which are not mirror image isomers are __________.
23) Is it theoretically possible to separate the pair of compounds below by distillation? Explain
briefly.
CH3
CH3
Br
Br
25) How many enantiomers are there of the molecule shown below?
OH
OH
A. 6 B. 2 C. 0 D. 1 E. 3
26) Which of the following terms best describes the pair of compounds shown: enantiomers,
diastereomers, or the same compound?
Cl
H3C
Cl
H
CH3
Cl
Cl
27) Which of the following terms best describes the pair of compounds shown: enantiomers,
diastereomers, or the same compound?
CH3
Br
H3C
H
CH2CH3
Br
CH2CH3
28) Label each asymmetric carbon in the molecule below as having the R or S configuration.
HO2C
F
H
H
H3C CH2CH3
ANSWERS
1) achiral
2) achiral
3) achiral
4) achiral
5) chiral
6) the same compound
7) enantiomers
8)
9)
10)
11)
12)
13)
14) 1
15) 5
16) 2
17) 1
18) No
19) Yes
20) No
21)
22) diastereomers
23) Yes. The molecules are related as diastereomers and hence have different boiling points.
24)
25) C
26) the same compound
27) enantiomers
28)
HO2C
F
H
s
H3C CH2CH3