Chapter 5: Q.18 (page 192)
Compounds E and F are two isomers of 2,3-dibromopentane drawn in staggered conformations. Which compounds (A–D) in Figure 5.8 are identical to E and F?

Short Answer
E and C, F and A are identical.
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Chapter 5: Q.18 (page 192)
Compounds E and F are two isomers of 2,3-dibromopentane drawn in staggered conformations. Which compounds (A–D) in Figure 5.8 are identical to E and F?

E and C, F and A are identical.
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How are the compounds in each pair related to each other? Are they identical, enantiomers, diastereomers, constitutional isomers, or not isomers of each other?
a.
and 
b.
and 
c.
and
d.
and 
e.
and 
f.
and 
Saquinavir (trade name Invirase) is a protease inhibitor, used to treat HIV (human immunodeficiency virus).

Locate the stereogenic centers in each drug.

a.

b.

c.
Cellulose is water insoluble, despite its many OH groups. Considering its three-dimensional structure, why do you think this is so?
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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