Chap07 - Stereochemistry I. Structural (constitutional) A....

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Stereochemistry Isomerism I. Structural (constitutional) A. Functional B. Positional C. Skeletal II. Stereo A. Geometric 1. Cis (Zusammen) 2. Trans (Entgegen) B. Conformational 1. Syn 2. Anti 3. Gauche C. Optical 1. 2. Diastereomers 3. Meso compounds
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Optical Isomers Optical isomers can only occur when at least one carbon atom in a molecule lives next to four different kinds of neighbors. H C OH CO 2 H CH 3 I'm a diversity Rainbow kinda guy- I like having as many different kinds of neighbors as possible. What a shame we only get four sticks in this life!!
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One day, after lamenting his misfortune at having such limited choices, Mr. Rainbow happens to look in a mirror and is absolutely delighted at what he sees. H C OH CO 2 H CH 3 C H 3 C OH CO 2 H H looking glass Omigod! Another guy who's just like me, but different somehow! I just have to climb onto the chimney-piece so I can go through the looking glass (Lewis Carroll) to meet him!
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C H 3 C OH CO 2 H H C OH CO 2 H CH 3 H looking glass After hours of fascinating political discussion with his enantiomer Mr. Rainbow discovers to his delight that he and his enantiomer see the world from very slightly different points of view. He tends to twist everything slightly to the left (even light!) and his enantiomer tends to twist everything slightly to the right (remember in the world through the looking glass everything is reversed- liberals there are politically to the right of center)!
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Scientific term for a rainbow carbon is chiral carbon . Enantiomers exist when rainbow molecules can look in mirror and see someone subtly different than themselves. Not all molecules with chiral carbons have enantiomers. All molecules having only one chiral carbon do have enantiomers. Chiral carbons must have four different neighbors (sometimes difference can be very subtle). The Polarimeter Suppose you work for the FB m I (Federal Bureau of molecule Inspection). You have a hot tip that a gang of extremist chiral molecules is planning a million molecule
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march on Washington, DC. (demanding four sticks for everybody).
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How do you detect the extremely chiral molecules and know who to spy on before the gang marches on Washington? The answer: use polarized light. FB m I agents always wear polarized sunglasses (even at night) so they can detect extremist chiral molecules. How does this work? The FB
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Chap07 - Stereochemistry I. Structural (constitutional) A....

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