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H CH3 CH2 (R)-BINAP-Ru pressure COOH COOH + H2 H3CO H3CO (S)-Naproxen (ee > 98%) PPhg Ph = C6H5 %3D BINAP

Principles of Instrumental Analysis

7th Edition

ISBN:9781305577213

Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch

Publisher:Douglas A. Skoog, F. James Holler, Stanley R. Crouch

Chapter28: High-performance Liquid Chromatography

Section: Chapter Questions

Problem 28.14QAP

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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.What kind of isomers are the enantiomers of BINAP?

H CH3
CH2
(R)-BINAP-Ru
pressure
COOH
COOH + H2
H3CO
H3CO
(S)-Naproxen
(ee > 98%)
PPhg
Ph = C6H5
%3D
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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