Chapter05notes

Chapter05notes - Stereochemistry v A chiral object is one...

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1 v A chiral object is one that cannot be superposed on its mirror image Stereochemistry
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2 1. Distinguish between Constitutional Isomers and Stereoisomers Isomers are different compounds with the same molecular formula. ________________________ have different IUPAC names same or different functional groups different physical properties different chemical properties ___________________ have : the same IUPAC names, except for prefix like cis or trans same functional groups same physical and chemical properties, except those related to 3-D shape different configurations (orientation in 3D space)
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3 1. Constitutional Isomers Molecular Formula Constitutional Isomers C2H6O C4H8O2
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4 Thalidomide N NH O O O O N NH O O O O enantiomer of Thalidomide (causes birth defects) (cures morning sickness) In 1963 it was discovered that thalidomide (sold as a mixture of both enantiomers) was the cause of horrible birth defects in many children born subsequent to the use of the drug 1. Stereoisomers
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5 2. Stereochemistry Definitions v Stereoisomers can be subdivided into two general categories: enantiomers & diasteromers e.g. (trans) Ph Ph Ph Ph (cis) and Cl H Cl H H Cl Cl H (trans) (cis) and __________________ stereoisomers whose molecules are non- superposable mirror images of each other ____________________ – stereoisomers whose molecules are not mirror images of each other
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6 We can now consider several molecules to determine whether or not they are chiral . 2. Achiral Molecules
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7 The molecule labeled A and its mirror image labeled B are not superimposable. No matter how you rotate A and B, all the atoms never align. Thus, CHBrClF is a chiral molecule, and A and B are different compounds. A and B are stereoisomers—specifically, they are _________________ . A carbon atom with four different groups is a tetrahedral chirality center . 2. Chiral Molecules
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In general, a molecule with no chirality centers will not be chiral. With one chirality center, a molecule will always be chiral. With two or more chirality centers, a molecule may or may not be chiral ( we will return to this later). For a molecule with
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This note was uploaded on 11/09/2011 for the course CHEM 2341 taught by Professor Staff during the Fall '11 term at Texas State.

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Chapter05notes - Stereochemistry v A chiral object is one...

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