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Naproxen, sold under the brand name Aleve among others, is a nonsteroidal anti- inflammatory drug (NSAID) used to treat pain (e.g. menstrual pains), inflammatory diseases such as rheumatoid arthritis, and fever. It is taken orally. The most potent enantiomer (the (S)-enantiomer) is produced by an asymmetric catalytic hydrogenation using Noyori's BINAP- ligand and ruthenium: CH3 COOH H2. [Ru(OAc),BINAP] coOOH MeO Meo (S)-Naproxen, 97% ee PPh PPH2 (R)-BINAP (i): After the reaction has completed analysis shows that the reaction mixture contains 392 g of (S)-naproxen (Mw 230,26 g/mol). How much of the (R)-enantiomer is expected to have been formed when the enantiomeric excess is 97% for the reaction? (ii): Explain briefly why the %enantiomeric excess can be regarded as a key green metric.

Naproxen, sold under the brand name Aleve among others, is a nonsteroidal anti- inflammatory drug (NSAID) used to treat pain (e.g. menstrual pains), inflammatory diseases such as rheumatoid arthritis, and fever. It is taken orally. The most potent enantiomer (the (S)-enantiomer) is produced by an asymmetric catalytic hydrogenation using Noyori's BINAP- ligand and ruthenium: CH3 COOH H2. [Ru(OAc),BINAP] coOOH MeO Meo (S)-Naproxen, 97% ee PPh PPH2 (R)-BINAP (i): After the reaction has completed analysis shows that the reaction mixture contains 392 g of (S)-naproxen (Mw 230,26 g/mol). How much of the (R)-enantiomer is expected to have been formed when the enantiomeric excess is 97% for the reaction? (ii): Explain briefly why the %enantiomeric excess can be regarded as a key green metric.

Organic Chemistry
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter22: Reactions Of Benzene And Its Derivatives
Section: Chapter Questions
Problem 22.59P
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(A): Naproxen, sold under the brand name Aleve among others, is a nonsteroidal anti- inflammatory drug (NSAID) used to treat pain (e.g. menstrual pains), inflammatory diseases such as rheumatoid arthritis, and fever. It is taken orally. The most potent enantiomer (the (S)-enantiomer) is produced by an asymmetric catalytic hydrogenation using Noyori's BINAP- ligand and ruthenium: CH3 Ha Ru(OAc),BINAP) COOH COOH Meo Meo PPH2 (S)-Naproxen, 97% 00 PPH2 (R)-BINAP (i): After the reaction has completed analysis shows that the reaction mixture contains 392 g of (S)-naproxen (Mw = 230,26 g/mol). How much of the (R)-enantiomer is expected to have been formed when the enantiomeric excess is 97% for the reaction? (ii): Explain briefly why the %enantiomeric excess can be regarded as a key green metric.
Transcribed Image Text:(A): Naproxen, sold under the brand name Aleve among others, is a nonsteroidal anti- inflammatory drug (NSAID) used to treat pain (e.g. menstrual pains), inflammatory diseases such as rheumatoid arthritis, and fever. It is taken orally. The most potent enantiomer (the (S)-enantiomer) is produced by an asymmetric catalytic hydrogenation using Noyori's BINAP- ligand and ruthenium: CH3 Ha Ru(OAc),BINAP) COOH COOH Meo Meo PPH2 (S)-Naproxen, 97% 00 PPH2 (R)-BINAP (i): After the reaction has completed analysis shows that the reaction mixture contains 392 g of (S)-naproxen (Mw = 230,26 g/mol). How much of the (R)-enantiomer is expected to have been formed when the enantiomeric excess is 97% for the reaction? (ii): Explain briefly why the %enantiomeric excess can be regarded as a key green metric.
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