Chapter5 - Chapter 5 1 Chapter 5 Stereochemistry: Chiral...

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Unformatted text preview: Chapter 5 1 Chapter 5 Stereochemistry: Chiral Molecules Chapter 5 2 Isomerism: Constitutional Isomers and Stereoisomers Stereoisomers are isomers with the same molecular formula and same connectivity of atoms but different arrangement of atoms in space Chapter 5 3 Enantiomers: stereoisomers whose molecules are nonsuperposable mirror images Diastereomers: stereoisomers whose molecules are not mirror images of each other Example: cis and trans double bond isomers Example: cis and trans cycloalkane isomers Chapter 5 4 Enantiomers and Chiral Molecules Chiral molecule Not superposable on its mirror image Can exist as a pair of enantiomers Pair of enantiomers A chiral molecule and its mirror image Achiral molecule Superposable on its mirror image Chapter 5 5 Example: 2-butanol I and II are mirror images of each other (figures a and b) I and II are not superposable and so are enantiomers (figure c) 2-butanol is a chiral molecule Example: 2-propanol Not chiral Chapter 5 6 Chiral molecule A molecule with a single tetrahedral carbon bonded to four different groups will always be chiral A molecule with more than one tetrahedral carbon bonded to four different groups is not always chiral Switching two groups at the tetrahedral center leads to the enantiomeric molecule in a molecule with one tetrahedral carbon Stereogenic center An atom bearing groups of such nature that an interchange of any two groups will produce a stereoisomer Carbons at a tetrahedral stereogenic center are designated with an asterisk (*) Example: 2-butanol Chapter 5 7 The Biological Importance of Chirality The binding specificity of a chiral receptor site for a chiral molecule is usually only favorable in one way Chapter 5 8 Tests for Chirality: Planes of Symmetry Plane of symmetry An imaginary plane that bisects a molecule in such a way that the two halves of...
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Chapter5 - Chapter 5 1 Chapter 5 Stereochemistry: Chiral...

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