Amygdalin, a compound isolated from the pits of apricots, peaches, and wild cherries, is
Chapter 5, Problem 5.65(choose chapter or problem)
Amygdalin, a compound isolated from the pits of apricots, peaches, and wild cherries, is sometimes called laetrile. Although it has no known therapeutic value, amygdalin 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. O OH HO OH O CN O O OH OH HO HO amygdalin COOH OH mandelic acid HCl, H2O only one of the products formed a. How many stereogenic centers are present in amygdalin? What is the maximum number of stereoisomers possible? b. Draw both enantiomers of mandelic acid and label each stereogenic center as R or S. c. Pure (R)-mandelic acid has a specifi c 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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