Additional Problems

7.16 Assign the conguration of these compounds as R or S:

7.17 Draw the structures of these compounds:
a) (R)-3-Chloro-1-pentene
b) (S)-1-Methyl-2-cyclohexenol
7.18 Determine the number of stereoisomers for these compounds:
b)
CH
2
CH
3
CH
2
CH
3
a)
O
OH
i)
CH
2
Ph
CO
2
H
Phenylalanine
H
2
NH
W
W
W
h)
H
W
W
W
CH
2
CH
2
Cl
HOCH
3 g)
O
X
CH
W
W
W
CH
3
HOH
Br
OH
H
f) e)

C
H
H
3
C
X
O
CH
d)
Br
c) C

HCPC
HOCH
2
CH
3
H
b)
CH
3
CO
2
H
a)
CH
3
O
ADDITIONAL PROBLEMS 249
Assess your understanding of
this chapters topics with
additional quizzing and
conceptual-based problems at
http://now.brookscole.com/
hornback2
BioLink
Openmirrors.com
7.19 Draw all of the stereoisomers of these compounds:
7.20 Explain whether or not these compounds would rotate plane-polarized light:
7.21 Consider the two enantiomers of this carboxylic acid:
CH
3
CHCOH
O
X W
Cl
i)
CH
3
W
W
W
W
W
CH
3
HOH
HOH
h)
CH
3
W
W
W
W
W
CH
3
HOH
HOH
g)
CH
3
CH
3
H
3
C
H
3
C
f)
CH
3
CH
3
H
3
C
H
3
C
e)
CH
3
CH
3
H
3
C
H
3
C
d)
Cl
Cl
H
H H
3
C
CH
3
CC

c)
OH
OH
b)
OH
OH
a)
OH
OH
b) CH
3
CHCHCHCHCHCH
3
W
OH
a) CH
3
CHCHCHCH
3
W
OH
d)
OH
c)
O
OH
250 CHAPTER 7 STEREOCHEMISTRY II
Explain whether each of the following statements is true, is false, or cannot be
determined from this information:
a) The enantiomers have the same melting point.
b) The enantiomers have the same boiling point.
c) The enantiomers have the same solubility in water.
d) The enantiomers have the same magnitude of rotation of plane-
polarized light.
e) The enantiomers have the same direction of rotation of plane-
polarized light.
f ) The enantiomers have the same pK
a
.
g) The enantiomers have the same rate of reaction with methanol.
h) The enantiomers have the same pH of an aqueous solution.
i) The enantiomers have the same rate of reaction with (S)-2-butanol.
j) The (R)-enantiomer rotates plane-polarized light in a clockwise
direction.
k) This reaction produces more of the (R)-enantiomer than the (S)-enantiomer.
7.22 Identify these pairs of compounds as identical, structural isomers, enantiomers,
or diastereomers:
i)
h)
g)
f) e)
d)
OH OH
OH OH
c)
OH
OH OH
OH
b)
Cl Cl
a)
Cl
Cl
CH
3
CHCOH
O
X
H
W
Cl
2
HCl C

CO
2
H
H
Cl
H
3
C
C

CO
2
H
H
Cl
H
3
C
ADDITIONAL PROBLEMS 251
Openmirrors.com
7.23 Identify these pairs of compounds as identical, structural isomers, enantiomers,
or diastereomers:
7.24 a) A solution of 0.2 g/mL of a compound in a 1 dm cell rotates plane-polarized
light 13.3 at the sodium D line. What is the specic rotation of this
compound?
b) What is the rotation caused by a solution of 0.1 g of this compound in 10 mL
of solution?
c) Suppose a solution of a compound gave a rotation of 160. How could
this rotation be distinguished from one of 200? from one of 520?
7.25 Describe how this amine could be resolved by using this carboxylic acid:
7.26 An unknown compound, X, has the formula C
6
H
12
.
a) Calculate the degree of unsaturation of X.
b) X reacts with H
2
in the presence of a catalyst to form a compound, Y, with
the formula C
6
H
14
. What information does this experiment provide about
the structure of X?
c) X rotates plane-polarized light, but Y does not. Show structures for
X and Y.
CNH
2
CH
3
W
W
H

W
C
Cl
H
3
C
H
CO
2
H
g)
CH
3
CO
2
H
CH
3
CO
2
H
H
2
NH
W
W
W
H C NH
2
f)
O
X
CH
W
W
W
CH
3
HOH
O
X
CH
W
W
W
H
H
3
COH e)
O
X
CH
W
W
W
CH
3
HOH
CH
3
W
W
W

CH
X
O
HOH
d)
O
X
CH
W
W
W
CH
3
HOH
OH
W
W
W
H
HCCH
3
O
X
c)
CH
3
W
W
W
W
W
CH
3
HCl
BrH
CH
3
W
W
W
W
W
CH
3
HCl
BrH
b)
CH
3
W
W
W
W
W
CH
3
HCl
BrH
CH
3
W
W
W
W
W
CH
3
HCl
HBr
a)
CH
3
W
W
W
W
W
CH
3
HOH
HOH
CH
3
W
W
W
W
W
CH
3
HOH
HOH
252 CHAPTER 7 STEREOCHEMISTRY II
7.27 How many stereoisomers exist for this compound? Assign the relative stabili-
ties of each. Is the methyl group axial or equatorial in the more stable con-
former of the least stable stereoisomer?
7.28 Draw a stereoisomer of this compound that is chiral, and draw two that are not
chiral:
7.29 Many compounds are found as a single stereoisomer in nature even though
they have numerous chirality centers. Determine how many chirality centers
are present in each of the following naturally occurring compounds and how
many stereoisomers are possible for each:
c)
OH
OH
OH
OH
Pancratistatin
(an anticancer drug)
O
NH
O
O
HO
b)
O
HO
HO
OH
OH
OH
OH
O
OH
OH
O
Sucrose
(table sugar)
CH
3
O
Alanine
residue
Phenylalanine
residue
(a tripeptide)
Threonine
residue
O CH
2
CHCH
3
W W
Ph OH
W W
W X X
a)
NH
2
CHCNHCHCNHCHCO
2
H
OH HO
CH
3
CH
3
Ph
ADDITIONAL PROBLEMS 253
BioLink
Openmirrors.com
Ascorbic acid
(vitamin C)
HO OH
O O CHCH
2
OH
OH
h)
g)
Vitamin D
2
HO
f)
Vitamin E
O
CH
3
CH
3
H
3
C
HO
PGE
2
(a prostaglandin)
O
HO
CO
2
H
OH
e)
d)
Testosterone
(a steroidal hormone)
OH
O
254 CHAPTER 7 STEREOCHEMISTRY II
7.30 All naturally occurring amino acids have the same relative conguration. All
have the S absolute conguration, except for cysteine, which has the R congu-
ration. Explain.
7.31 Explain whether each of these compounds is chiral or not:
f)
CH
3
O
O
S

..
e)
Ph
CH
3
CH
2
CH
3
CH
2
Br

+
NCH
2
CH
3

d)
H
3
C CO
2
H
CH
3
O CO
2
H
c)
H
3
C CH
3
CH
3
O CO
2
H
b)
CCC

H
H
3
C
COH
CH
3
O
X
a)
CCC

H
3
C
H
3
C
CCH
3
H
O
X
CO
2
H
Cysteine
CH
2
SH
C H H
2
N
i)
Apoptolidin
(a potent antitumor agent)
O
O
O
O
O
O
O
O
O
OH
OH
OH
H H
OH
HO
HO
HO
O
O
O
OH
O
ADDITIONAL PROBLEMS 255
BioLink
Openmirrors.com