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Organic Chemistry Problems
Organic Chemistry Problems
PROBLEMS
30. Which of the following have an asymmetric center?
CHBr2Cl
CH2FCl
CH3CHCl2
CHFBrCl
CH3CH2CHClCH3
31. Disregarding stereoisomers, give the structures of all compounds with molecular formula C5H10. Which ones can exist as
stereoisomers?
32. Draw all possible stereoisomers for each of the following compounds. Indicate if no stereoisomers are possible.
a.
b.
c.
d.
2-bromo-4-methylpentane
2-bromo-4-chloropentane
3-heptene
1-bromo-4-methylcyclohexane
e.
f.
g.
h.
1-bromo-3-chlorocyclobutane
2-iodopentane
3,3-dimethylpentane
3-chloro-1-butene
33. Name the following compounds using R,S and E,Z designations where necessary:
CH(CH3)2
F
I
F
H
a.
C
Cl
b.
C
Br
C
H3C
CH2CH3
H
c.
d.
C
Br
Cl
CH3
C CH CH Cl
2
2
CH3CH2 H
34. Mevacor is used clinically to lower serum cholesterol levels. How many asymmetric centers does it have?
HO
O
O
O
O
CH3
H3C
CH3
Mevacor
Br
OH
CH3
36. Indicate whether the following pairs of structures represent identical compounds, enantiomers, diastereomers, or constitutional
isomers:
H
CH3
CH3
H3C
H3C
H
H
CH3
a.
C C
C C
e.
and
and
H
CH3
H
CH3
H
Br
Br
H3C
CH2OH
b.
C
H
CH2CH3
and
CH3
CH2CH3
C
H3C
CH2OH
f.
H
CH2OH
C
Cl
CH2CH3
c.
Cl
CH3
CH2CH3
H3C
g.
and
CH3
and
C CH OH
2
CH3CH2 CH
3
C
H3C
and
C
Br
C
Br
CH3
d.
H H
Cl Cl
and
H 3C
Cl H
C
CH3
CH3
CH3
h.
H Cl
CH3
CH3
and
H3C
37. a. Give the product(s) that would be obtained from the reaction of cis-2-butene with each of the following reagents. If the
products can exist as stereoisomers, show which stereoisomers are formed.
4. CH 3OH + acid
1. HCl
2. H 2O + acid
3. H2, Pt>C
b. How would the product(s) differ if the reactant had been trans-2-butene?
38. Which of the following compounds have an achiral stereoisomer?
a. 2,3-dichlorobutane
b. 2,3-dichloropentane
c. 2,4-dibromopentane
d. 2,3-dibromopentane
39. Draw the stereoisomers of 2,4-dichlorohexane. Indicate pairs of enantiomers and pairs of diastereomers.
40. Give the products of the following reactions. If the products can exist as stereoisomers, show which stereoisomers are formed.
a. 1-butene + HCl
b. cis-2-pentene + HCl
c. 1-ethylcyclohexene + H 2O + acid
41. A solution of an unknown compound (3.0 g of the compound in 20 mL of solution), when placed in a polarimeter tube 2.0 dm
long, was found to rotate the plane of polarization of polarized light 1.8 in a counterclockwise direction. What is the specific
rotation of the compound?
42. Butaclamol is a potent antipsychotic that has been used clinically in the treatment of schizophrenia. How many asymmetric centers
does it have?
OH
C(CH3)3
Butaclamol
e.
f.
g.
h.
an automobile
a wheelbarrow
a nail
a screw
46. The stereoisomer of naproxen that is the active ingredient in Aleve and in several other over-the-counter nonsteroidal antiinflammatory drugs is shown below. Is the active ingredient (R)-naproxen or (S)-naproxen?
CH3
C
COH
CH3O
O
(?)-naproxen
c. 3,4-dichlorohexane
a.
C
Br
H
CH2CH2CH3
b.
Br
Br
49. Citrate synthase, one of the enzymes in the series of enzyme-catalyzed reactions known as the citric acid cycle, catalyzes the
synthesis of citric acid from oxaloacetic acid and acetyl-CoA. If the synthesis is carried out with acetyl-CoA that has radioactive
carbon (14C) in the indicated position, the isomer shown here is obtained. (Note: 14C has a higher priority than 12C.)
O
HOOCCH2CCOOH
oxaloacetic acid
14
CH2COOH
O
+
citrate synthase
14
CH3CSCoA
C
HO
acetyl-CoA
COOH
CH2COOH
citric acid
HO
H
CH2OH
NHCCHCl2
O
NO2
chloramphenicol
51. For many centuries, the Chinese have used extracts from a group of herbs known as ephedra to treat asthma. Chemists have been
able to isolate a compound from these herbs, which they named ephedrine, a potent dilator of air passages in the lungs.
CH3
CHCHNHCH3
OH
ephedrine
HO
H
C NHCH3
CH3
52. Indicate whether the following pairs of structures represent identical compounds or enantiomers:
CH3
CH2CH3
CH3
CH3
H
H
OH
a. Cl
b. HO
H
H
CH3
C
C
C
C
and
and
C
C
C
C
H
Cl
CH3
H
Cl
H
H
Cl
CH2CH3
CH3
CH3
CH3
53. The following compound has only one asymmetric center. Why, then, does it have four stereoisomers?
CH3CH
CHCHCH3
OH
54. Two stereoisomers are obtained from the reaction of HBr with (S)-4-bromo-1-pentene. One of the stereoisomers is optically active,
and the other is not. Give the structures of the stereoisomers, indicating their configurations, and explain the difference in the
optical properties.
55. Indicate whether the following pairs of structures represent identical compounds, enantiomers, diastereomers, or constitutional
isomers:
a.
c.
and
b.
and
d.
and
and
CH3CHOH
b. 7
CH3CH2OCH3
CH3
2
CH(CH3)2
d.
CH
3. a. F, G, J, L, N, P, Q, R, S, Z b. A, C, D, H, I, M, O, T, U, V, W, X, Y
4. a, c, and f 6. a, c, and f
7. a.
Br
CH2OH
CH2OH
H
b.
CH3
H 3C
CH2CH2Cl
C
CH3CH2
c.
CH3
CH2CH3
CH3
CH2OH
CH
H3C
H
3
b.
CH(CH3)2
a.
CH2CH2Cl
H3 C
CH3
CH2CH2Br
3
CH2
Cl
CH2CH2CH2Br
CH2CH3
4
CH
C
CH3CH2
H
OH
HO
CH2CH3
OH
b.
2
CH2CH2OH
OH
CH3
3
CH2OH
CH2CH2CH3
C
CH3CH2
c.
H
Br
CH2CH2CH3
C
H
Br
CH2CH3
H H
CH3 CH3
CH3
Br
CH(CH3)2
HO
10.
9. a, b, and c
c.