208 Chapter 3 Stereochemistry - 1 Chapter 3 Stereochemistry...

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6/9/2016 1 Chapter 3 Stereochemistry 3.1 Molecular Chirality: Enantiomers 3.2 The Stereogenic Center 3.3 Symmetry in Achiral Structures 3.4 Properties of Chiral Molecules: Optical Activity 3.5 Absolute and Relative Configuration 3.6 The Cahn-Ingold-Prelog R- S Notational System 3.7 Fischer Projections 3.9 Reactions that Create a Stereogenic Center (with Chapter 6) 3.10 Chiral Molecules with Two Stereogenic Centers 3.11 Achiral Molecules with Two Stereogenic Centers 3.12 Molecules with Multiple Stereogenic Centers 3.13 Resolution of Enantiomers Every thing has a mirror image, but not all things are superimposable on their mirror images Some objects such as spoons, mug, cups, balls, chairs are superimposable on their mirror image and are said to be achiral 3.1 Molecular Chirality: Enantiomers Stereochemistry is chemistry in 3 dimensions, it is the study of the spatial arrangement of atoms and molecules, it deals with how atoms in a molecule are arranged in space. Some objects such as hands, gloves, feet, shoes are not the same as their mirror image. These objects are said to be chiral They have a “left” and a “right” version
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6/9/2016 2 A molecule is chiral if its two mirror image forms are not superpimposable upon one another. Chirality in Molecules Molecules exist as three-dimensional objects sp 3 hybridized C is tetrahedral A molecule is achiral if its two mirror image forms are superimposable . Br Cl H F Bromochlorofluoromethane is chiral H Cl Br F To show nonsuperimposability, rotate this model 180° around a vertical axis. It cannot be superimposed point for point on its mirror image.
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6/9/2016 3 Br Cl H F Bromochlorofluoromethane is chiral H Cl Br F H and F substituents match up, Cl and Br don’t are enantiomers with respect to each other and Chiral molecules exist as a pair of enantiomers Enantiomers are related to each other like right hand is related to left hand Enantiomers are nonsuperimposable mirror images Enantiomers
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