Chapter 5: Q.38 (page 206)
Label each pair of compounds as constitutional isomers, stereoisomers, or not isomers of each other.




Short Answer
- Stereoisomers
- Constitutional isomers
- Not isomers of each other
Not isomers of each other
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Chapter 5: Q.38 (page 206)
Label each pair of compounds as constitutional isomers, stereoisomers, or not isomers of each other.




Not isomers of each other
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Classify each pair of compounds as constitutional isomers or stereoisomers.




Locate the tetrahedral stereogenic center(s) in each compound. A molecule may have one or more stereogenic centers.

a.

b.

c.

d.

e.

f.
Draw both enantiomers for each biologically active compound.

amphetamine
(a powerful central nervous stimulant)
a.

ketoprofen
(analgesic and anti-inflammatory agent)
b.
If the two stereogenic centers of a compound are R,S in configuration, what are the R,S assignments for its enantiomer and two diastereomers?
Amygdalin, a compound isolated from the pits of apricots, peaches, and wild cherries, has been used as an unsanctioned anticancer drug both within and outside of the United States. One hydrolysis product formed from amygdalin is mandelic acid, used in treating common skin problems caused by photo-aging and acne.

a. How many stereogenic centres are present in amygdalin? What is the maximum number of stereoisomers possible?
b. Draw both enantiomers of mandelic acid and label each stereogenic centre as R or S.
c. Pure (R)-mandelic acid has a specific rotation of –154. If a sample contains 60% of the R isomer and 40% of its enantiomer, what is of this solution?
d. Calculate the ee of a solution of mandelic acid having = +50. What is the percentage of each enantiomer present?
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