lecture 12 F08 given - Lecture 12 Organic Chemistry I Prof....

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Organic Chemistry I 310/318M Pre-Health Professionals Unique numbers: 54410, 54435, 54440, 54445, and 54655 Prof. Jonathan L. Sessler Lecture 12 Note: Homework 2 due today; give it to one of the TA’s, please Note: Homework 3 due next Wednesday Note: Exam 1 is next Thursday evening; it will cover chapts. 1-3, inclusive
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Stereoisomerism and Chirality Chapter 3.
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• Thalidomide - sedative Î birth defects only because S and R forms (enantiomers) given as a mixture. Pure R form (show on right) would probably have not created a problem. • Thalidomide S enantiomer (bad one) is now being used for MS. • Must be rigorously avoided by women of child-bearing age! We’ll learn what R and S mean soon. For now, just know they are a way to designate the specific nature of a special kind of isomerism involving the “handedness” of molecules, called stereoisomerism. N N H O O H O O N N H O O H O O (R) (S) Thalidomide: Why chirality matters
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Isomers Isomers: Isomers: Different compounds with the same molecular formula. Constitutional isomers: Constitutional isomers: Isomers with a different connectivity. Stereoisomers Stereoisomers : Isomers with the same connectivity but a different orientation of their atoms in space. Configurational Configurational isomers: isomers: Isomers made by making or breaking bonds. If this is done for the same substituents at the same atom, we don’t have constitutional isomers, but we may have stereoisomers. Conformational isomers: Conformational isomers: Isomers produced by bond rotations. If rotation is restricted, we can produce stereoisomers.
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Chirality Chiral Chiral : : From the Greek, cheir , hand – an object that is not superposable on its mirror image. Achiral Achiral : : An object that lacks chirality; one that lacks handedness . – An achiral object has at least one element of symmetry. – Plane of symmetry: Plane of symmetry: An imaginary plane passing through an object dividing it so that one half is the mirror image of the other half. – Center of symmetry: Center of symmetry: A point so situated that identical components of the object are located on opposite sides and equidistant from that point along any axis passing through it.
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lecture 12 F08 given - Lecture 12 Organic Chemistry I Prof....

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