Chapter 5 Stereochemistry Adel M. Awadallah Islamic University of Gaza

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Chapter 5 Stereochemistry Adel M. Awadallah Islamic University of Gaza Organic chemistry for medicine and biology students Chem 2311 Chapter 5 Stereochemistry By Prof. Dr. Adel M. Awadallah Islamic University of Gaza

Stereochemistry Isomers: different compounds having the same molecular formula

A chiral molecule is one that is optically active A racemic mixture (racemic modification) is one with equal ratios of enantiomers (50:50 mixture)

Configuration and the R-S Convention

Examples

Compounds with more than one stereogenic center; (Diasteriomers)

Properties of enantiomers and diastereomers A) Enantiomers Have the same physical properties except for direction of rotation of plane polarized light Have the same chemical properties except for their reaction with other chiral molecules (This usually seen in their biological activity) B) Diastereomers Have different physical properties Similar chemical properties

Chemical reactions of stereoisomers 1) Generation of a chiral center

Reaction away from a chiral center

Generation of a second chiral center

Resolution of enantiomers Enantiomers + chiral molecules gives diasteriomers which can be sepearated, then we get red of the chiral molecules