Chapter 5: Q.24 (page 195)
a. Label the four stereogenic centres in sorbitol as R or S.
b. How are sorbitol and A related?
c. How are sorbitol and B related?



Short Answer
a.



b. Diastereomers.
c. Enantiomers.
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Chapter 5: Q.24 (page 195)
a. Label the four stereogenic centres in sorbitol as R or S.
b. How are sorbitol and A related?
c. How are sorbitol and B related?



a.



b. Diastereomers.
c. Enantiomers.
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Locate the stereogenic centers in each compound.

a.

b.
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?
a) Locate the stereogenic centers in the ball-and-stick model of ezetimibe (trade name Zetia), a cholesterol-lowering drug. (b) Label each stereogenic center as R or S.

Draw all possible stereoisomers for each compound. Label pairs of enantiomers and diastereomers.

a.

b.

c.
Rank the following groups in order of decreasing priority.
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