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Chapter 5 Notes - Chapter5 Stereochemistry ChiralMolecules...

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Chapter 5 Stereochemistry: Chiral Molecules
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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.
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Enantiomers: stereoisomers whose molecules are nonsuperposable mirror images of each other. Diastereomers : stereoisomers whose molecules are not mirror images of each other. Example: cis and trans double bond isomers‐ stereoisomers that are diastereomers Example: cis and trans cycloalkane isomers
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Enantiomers and Chiral Molecules Chiral molecule: a molecule which is not superposable on its mirror image. A chiral molecule and its mirror image are called a pair of enantiomers . Molecules that are superposable on their mirror image are achiral. Example: 2‐butanol is a chiral molecule. I and II are mirror images (figures a and b) and are not superposable (figure c). They are enantiomers.
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Example: 2‐propanol, in contrast, is not chiral. A pair of enantiomers is always possible for molecules that contain a single tetrahedral atom with four different groups attached to it. Such atoms are called chirality centers . 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. Any atom at which an interchange of groups produces a stereoisomer is called a stereogenic center . Carbons at a tetrahedral stereogenic center are designated with an asterisk (*). Example: 2‐butanol
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The Biological Importance of Chirality The binding specificity of a chiral receptor site for a chiral molecule is usually only favorable in one way.
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Chiral molecules can exhibit their handedness in many ways.
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Tests for Chirality : Planes of Symmetry
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