1 / 26

Exploring Stereochemistry: Enantiomers, Chirality & Properties

Understand stereochemistry, enantiomers, and chiral properties in molecules through examples and definitions. Learn about chiral drugs, structures, and the implications of molecular arrangement in space.

mountain
Download Presentation

Exploring Stereochemistry: Enantiomers, Chirality & Properties

An Image/Link below is provided (as is) to download presentation Download Policy: Content on the Website is provided to you AS IS for your information and personal use and may not be sold / licensed / shared on other websites without getting consent from its author. Content is provided to you AS IS for your information and personal use only. Download presentation by click this link. While downloading, if for some reason you are not able to download a presentation, the publisher may have deleted the file from their server. During download, if you can't get a presentation, the file might be deleted by the publisher.

E N D

Presentation Transcript

  1. Chapter 5 Stereochemistry The Arrangement of Atoms in Space; The Stereochemistry of Addition Reactions

  2. Molecular Chirality: Enantiomers

  3. Chirality A molecule is chiral if its two mirror image forms are not superimposable upon one another. A molecule is achiral if its two mirror image forms are superimposable.

  4. Bromochlorofluoromethane is chiral It cannot be superimposed point for point on its mirror image. Cl Br H F

  5. Bromochlorofluoromethane is chiral To show nonimsuperposability, rotate this model 180° around a vertical axis. Cl Cl Br Br H H F F

  6. Enantiomers Chirality & nonsuperimposable mirror images

  7. Isomers constitutional isomers stereoisomers

  8. Isomers constitutional isomers stereoisomers enantiomers diastereomers

  9. Physical Properties of Enantiomers

  10. Properties of enantiomers Physical properties are the same: melting point, boiling point, density, etc Some others are different: properties that depend on the shape of molecule eg. biological-physiological and optical properties.

  11. Odor CH3 CH3 O O H3C H3C CH2 CH2 (–)-Carvonespearmint oil (+)-Carvonecaraway seed oil

  12. H H3C CH2CH(CH3)2 C C HO O Chiral drugs Ibuprofen is chiral, but normally sold asa racemic mixture. The enantiomer belowis the one responsible for its analgesic and antiinflammatory properties.

  13. A Sedative or a Potent Teratogen?

  14. w x y C z The chiral carbon atom a carbon atom with fourdifferent groups attached to it also called: chiral center; chiral carbonasymmetric center asymmetric carbonstereocenter stereogenic center

  15. C Chirality and chiral carbons A molecule with a single stereogenic center is chiral. 2-Butanol is an example. H CH3 CH2CH3 OH

  16. CH3 CH2CH2CH2CH3 CH3CH2CH2 C CH2CH3 Examples of molecules with 1 chiral carbon a chiral alkane

  17. OH Examples of molecules with 1 chiral carbon Linalool, a naturally occurring chiral alcohol

  18. H2C CHCH3 O Examples of molecules with 1 chiral carbon attached to the chiral carbon are: —H —CH3 —OCH2 —CH2O 1,2-Epoxypropane: a chiral carbon can be part of a ring

  19. CH3 H C CH2 CH3 Examples of molecules with 1 chiral carbon Limonene: a chiral carbon can be part of a ring attached to thechiral carbon are: —H —CH2CH2 —CH2CH= —C=

  20. H CH3 D C T Examples of molecules with 1 chiral carbon Chiral as a result of isotopic substitution

  21. A molecule with a single chiral carbonmust be chiral. But, a molecule with two or more chiral carbons may be chiral or it may not. We’ll return to this when we consider molecules with more than one chiral carbon atom.

More Related