Naproxen, a nonsteroidal anti-inflammatory drug that is the active ingredient in Aleve (p. 115), has a specific rotation of +66. One commercial preparation results in a mixture with a 97% enantiomeric excess. a. Does naproxen have the R or the S configuration? b. What percent of each enantiomer is obtained from the commercial preparation?

Naproxen, a nonsteroidal anti-inflammatory drug that is the active ingredient in Aleve (p. 115), has a specific rotation of +66. One commercial preparation results in a mixture with a 97% enantiomeric excess. a. Does naproxen have the R or the S configuration? b. What percent of each enantiomer is obtained from the commercial preparation?

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter4: Organic Compounds: Cycloalkanes And Their Stereochemistry

Section4.SE: Something Extra

Problem 59AP

See similar textbooks

Similar questions

Naproxen, a nonsteroidal anti-inflammatory drug that is the active ingredient in Aleve, has a specific rotation of +66. One commercial preparation results in a mixture with a 97% enantiomeric excess. a. Does naproxen have the R or the S configuration? b. What percent of each enantiomer is obtained from the commercial preparation?
Citalopram is an antidepressant pharmaceutical that is sold as a racemic mixture. However, it is known that the (S) enantiomer is 30x more biologically active than the (R) enantiomer. Draw the (S) configuration.
Trabectedin, shown in a ball-and-stick model on the cover of this text, is an anticancer drug sold under the trade name Yondelis. a. Locate the stereogenic centers in trabectedin. b.What is the maximum number of stereoisomers possible for trabectedin? c.Draw the enantiomer. d.Draw a diastereomer. e.If the specific rotation of trabectedin is +41.5, what is the [α] of a solution that contains 75% trabectedin and 25% of its enantiomer?f . What is the ee of a solution with [α] = +10.5?
Saquinavir (trade name Invirase) is a protease inhibitor, used to treat HIV (human immunodeficiency virus). a.Locate all stereogenic centers in saquinavir, and label each stereogenic center as R or S. b.Draw the enantiomer of saquinavir. c.Draw a diastereomer of saquinavir. d.Draw a constitutional isomer that contains at least one different functional group.
Part B. Mark each chirality center in each molecule with an asterisk (*).
Hypoglycin A, an amino acid derivative found in unripened lychee, is a compound that is acutely toxic and can lead to death when ingested in large amounts by undernourished children. Draw all possible stereoisomers for hypoglycin A, and give the R,S designation for each stereogenic center.
Captopril is a drug used to treat high blood pressure and congestive heart failure. a.Designate each stereogenic center as R or S. b.Draw the enantiomer of captopril. c.What product is formed when captopril is treated with one equivalent of NaH? d.What product is formed when captopril is treated with two equivalents of NaH?
Captopril is a drug used to treat high blood pressure and congestiveheart failure.Designate each stereogenic center as R or S.
For many centuries, the Chinese have used extracts from a group of herbs known as ephedra to treat asthma. A compound named ephedrine has been isolated from these herbs and found to be a potent dilator of air passages in the lungs. a. How many stereoisomers does ephedrine have? b. The stereoisomer shown here is the one that is pharmacologically active. What is the configuration of each of the asymmetric centers?
Exemestane (trade name Aromasin) is a drug used to treat breast cancer. Locate the stereogenic centers in exemestane and draw the enantiomer.
The [α] of a pure enantiomer is -39°. The observed rotation of a sample containing both enantiomers was found to be -0.62°. a) Calculate the enantiomeric excess (e.e %) b) Calculate the percent of each enantiomer present.
Eleostearic acid is an unsaturated fatty acid obtained from the seeds of the tung oil tree (Aleurites fordii), a deciduous tree native to China. (a) Draw the structure of a stereoisomer that has a higher melting point than eleostearic acid. (b) Draw the structure of a stereoisomer that has a lower melting point.