notes_14C_stereo02

notes_14C_stereo02 - STEREOCHEMISTRY: The Arrangement of...

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STEREOCHEMISTRY: The Arrangement of Atoms in Space History: (source: Hardinger; Thinkbook 14C: pgs11-13) Late 17 th century: Christiaan Huygens - discovers plane-polarized light, which is light that has been filtered so that the electromagnetic components lie in a single plane. 1815: Jean Baptiste Biot certain natural organic compounds are optically active or can rotate plane-polarized light clockwise (+ dextrorotatory) and counterclockwise (- levorotatory). Also discovered that racemic acid is optically inactive. 1874: Joseph Achille LeBel and Jacobus Henricus van’t Hoff - proposed that a molecule having a tetrahedral carbon atom (sp^3) with four different attachments may exist as a pair of isomers. Overview: Figure 5-1 Relations among isomers of various types. (Source: Vollhardt/ Schore’s Organic Chemistry –eBook, 5 th edition; Sec 5.1) I. ISOMERS: A) Constitutional isomers: Have the same molecular formula but differ in the way their atoms are connected. Ex:
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Isobutene n-butane C 4 H 10 C 4 H 10 B) Stereoisomers (Configurational Isomers): (source: Bruice 4 th edition; pg.182) Atoms are connected in the same way, but arranged differently in space 1)Enantiomers : - Molecules with same molecular formula, contain at least one chiral center , and are nonsuperimposable mirror images ( chiral ) of each other. *Note: Objects like the hand can be considered chiral because it’s not the same as its mirror image. - Contain similar physical properties except for the direction of polarizing light
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This note was uploaded on 07/27/2009 for the course CHEM 14C-14D taught by Professor Hardinger during the Fall '08 term at UCLA.

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notes_14C_stereo02 - STEREOCHEMISTRY: The Arrangement of...

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