SolomonsLKChapter5

SolomonsLKChapter5 - Chapter 5 Stereochemistry: Chiral...

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Stereochemistry: Chiral Molecules Chapter 5
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Constitutional Isomers = same molecular formula, different connectedness Stereoisomers = same molecular formula, same connectivity of atoms but different arrangement of atoms in space Isomerism: Constitutional Isomers and Stereoisomers
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Examples of Constitutional Isomers formula constitutional isomers C 3 H 8 O CH 3 CH 2 CH 2 OH CH 3 CHCH 3 C 4 H 10 CH 3 CH 2 CH 2 CH 3 CH 3 CHCH 3 OH CH 3 Constitutional Isomers - Review Same molecular formula – different bond connectivities Always different properties Very different properties if different functional groups
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Stereochemistry Although everything has a mirror image, mirror images may or may not be superimposable. Some molecules are like hands. Left and right hands are mirror images, but they are not identical, or superimposable . Chiral and Achiral Molecules
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Stereochemistry Other molecules are like socks. Two socks from a pair are mirror images that are superimposable. A sock and its mirror image are identical. A molecule or object that is superimposable on its mirror image is said to be achiral . Chiral and Achiral Molecules
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Stereochemistry We can now consider several molecules to determine whether or not they are chiral . Chiral and Achiral Molecules
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Mirror image = converts right hand into left
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Stereochemistry 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 enantiomers. A carbon atom with four different groups is a tetrahedral stereogenic center . Chiral and Achiral Molecules
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Stereochemistry Chiral and Achiral Molecules
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C H OH CH 3 CH 3 A C CH 3 H HO CH 3 B rotate 2- propanol is not chiral B is mirror image of A, but is superimposable by 180 o rotation Everything has a mirror image, the question is whether it is superimposable
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A chiral molecule: 2-butanol I and II are mirror images of each other I and II are not superimposable and so are enantiomers
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Stereochemistry To locate a chirality center, examine each tetrahedral carbon atom in a molecule, and look at the four groups— not the four atoms—bonded to it. Always omit from consideration all C atoms that are not tetrahedral. These include CH 2 and CH 3 groups Any sp or sp 2 hybridized C Chirality Centers (also called stereogenic centers)
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Larger organic molecules can have two, three or even hundreds of chirality centers. Chirality Centers
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SolomonsLKChapter5 - Chapter 5 Stereochemistry: Chiral...

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