Chapter09- Stereochemistry

Chapter09- Stereochemistry - 9. Stereochemistry Based on...

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9. Stereochemistry Based on McMurry’s Organic Chemistry , 6 th edition ©2002 Ronald Kluger Department of Chemistry University of Toronto
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McMurry Organic Chemistry 6th edition Ch 9 (c) 2 2 Stereochemistry Some objects are not the same as their mirror images (technically, they have no plane of symmetry) A right-hand glove is different than a left-hand glove (See Figure 9.1) The property is commonly called “handedness” Organic molecules (including many drugs) have handedness that results from substitution patterns on sp 3 hybridized carbon
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McMurry Organic Chemistry 6th edition Ch 9 (c) 2 3 Enantiomers – Mirror Images Molecules exist as three-dimensional objects Some molecules are the same as their mirror image Some molecules are different than their mirror image These are stereoisomers called enantiomers
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McMurry Organic Chemistry 6th edition Ch 9 (c) 2 4 9.1 Enantiomers and the Tetrahedral Carbon Enantiomers are molecules that are not the same as their mirror image They are the “same” if the positions of the atoms can coincide on a one-to-one basis (we test if they are superimposable , which is imaginary) This is illustrated by enantiomers of lactic acid
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McMurry Organic Chemistry 6th edition Ch 9 (c) 2 5 Examples of Enantiomers Molecules that have one carbon with 4 different substituents have a nonsuperimposable mirror image – enantiomer Build molecular models to see this
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McMurry Organic Chemistry 6th edition Ch 9 (c) 2 6 Mirror-image Forms of Lactic Acid When H and OH substituents match up, COOH and CH 3 don’t when COOH and CH 3 coincide, H and OH don’t
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McMurry Organic Chemistry 6th edition Ch 9 (c) 2 7 9.2 The Reason for Handedness: Chirality Molecules that are not superimposable with their mirror images are chiral (have handedness) A plane of symmetry divides an entire molecule into two pieces that are exact mirror images A molecule with a plane of symmetry is the same as its mirror image and is said to be achiral (See Figure 9.4 for examples)
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McMurry Organic Chemistry 6th edition Ch 9 (c) 2 8 Chirality If an object has a plane of symmetry it is necessarily the same as its mirror image The lack of a plane of symmetry is called “handedness”, chirality Hands, gloves are prime examples of chiral object They have a “left” and a “right” version
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McMurry Organic Chemistry 6th edition Ch 9 (c) 2 9 Plane of Symmetry The plane has the same thing on both sides for the flask There is no mirror plane for a hand
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McMurry Organic Chemistry 6th edition Ch 9 (c) 2 10 Chirality Centers A point in a molecule where four different groups (or atoms) are attached to carbon is called a chirality center There are two nonsuperimposable ways that 4 different different groups (or atoms) can be attached to one carbon atom If two groups are the same, then there is only one way A chiral molecule usually has at least one chirality center
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Chapter09- Stereochemistry - 9. Stereochemistry Based on...

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