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Chapter 5 Stereochemistry The Arrangement of Atoms in Space; The Stereochemistry of

Chapter 5 Stereochemistry The Arrangement of Atoms in Space; The Stereochemistry of Addition Reactions. Molecular Chirality: Enantiomers. Chirality. A molecule is chiral if its two mirror image forms are not superimposable upon one another.

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Chapter 5 Stereochemistry The Arrangement of Atoms in Space; The Stereochemistry of

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  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.

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