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CH2 H CH3 (R)-BINAP-Ru pressure COOH + H2 COOH H3CO H3CO (S)-Naproxen (ee > 98%) PPhg Ph = C6H5 BINAP

Introduction to General, Organic and Biochemistry

11th Edition

ISBN:9781285869759

Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Chapter31: Immunochemistry

Section: Chapter Questions

Problem 31.75P

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Concept explainers

Alkanes and Cycloalkanes

Alkanes are saturated organic compounds which are made up of C and H atoms. Alkanes have the general formula of CnH2n+2. Alkane contains sp3 hybridized carbon atoms with four sigmas (σ) bonds & every hydrogen atom is connected with one of the carbon atoms. The size of the alkane could be determined by the number of carbon atoms located in it.

Question

The chiral catalyst (R)-BINAP-Ru is used to hydrogenate alkenes to give alkanes . The products are produced with high enantiomeric excess. An example is the formation of (S)-naproxen, a pain reliever.

Q.How can one enantiomer of naproxen be formed in such high yield?

CH2
H
CH3
(R)-BINAP-Ru
pressure
COOH + H2
COOH
H3CO
H3CO
(S)-Naproxen
(ee > 98%)
PPhg
Ph = C6H5
BINAP

Definition Definition Simplest organic compounds that contain only single bonds between carbon – carbon atoms and carbon – hydrogen bonds. This means they are a series of saturated compounds with a general molecular formula, C n H 2n+2 .

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