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?

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?

EBK A SMALL SCALE APPROACH TO ORGANIC L

4th Edition

ISBN:9781305446021

Author:Lampman

Publisher:Lampman

Chapter92: Polarimetry

Section: Chapter Questions

Problem 3P

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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?
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 (*).
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A solution prepared by mixing 10 mL of a 0.10 M solution of the R enantiomer of a compound and 30 mL of a 0.10 M solution of the S enantiomer was found to have an observed specific rotation of +4.8. What isthe specific rotation of each of the enantiomers? (Hint: mL * M = millimole, abbreviated as mmol)
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Methylcyclohexane: Axial to Equatorial Interconversion 1) How does the methyl group substituent change the conformational preferences relative to unsubstituted cyclohexane? 2) How does the methyl group substituent affect the barrier for interconversion from one chair conformation to another? Does the methyl substituent freeze the ring from interconverting or significantly slow it down?
Assign R or S configurations to each stereogenic center of isoborneol and borneol. Give the relationship between these two stereoisomers.
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.
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?