6-StereochemistryHLSF07

6-StereochemistryHLSF07 - CHIRAL molecules: 1. Usually...

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CHIRAL molecules: 1. Usually contain 1 or more asymmetric carbons (often referred to as chirality centers, stereogenic centers, stereocenters) 2. Do NOT possess an internal plane of symmetry ACHIRAL molecules : 1. Molecules with 0 asymmetric carbons are achiral (CH 3 OH, CCl 4 ,CH 3 CH 2 Br) 2. Molecules with 2 or more asymmetric carbons are achiral if they contain an internal plane of symmetry (MESO). HO H H OH H H 3. Mirror image NON-SUPERIMPOSABLE 3. Mirror image SUPERIMPOSABLE
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Everything has a mirror image The big question: Are the two images the same or different? If the two images are superimposable then the two images are the same molecule. If a molecule and its mirror image are non-superimposable each individual molecule is CHIRAL and the two images are ENANTIOMERS . mirror Enantiomers = non-superimposable mirror image isomers.
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ISOMERS CONFORMATIONAL CONSTITUTIONAL STEREOISOMERS CONFIGURATIONAL cis/trans DIASTEREOMERS ENANTIOMERS
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2-bromobutane CH 3 CH 2 CH 3 Br H CH 3 CH 3 Br H 2-bromopropane mirror Notice what happens if you exchange any two groups
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Naming Stereocenters Recall Alkene Stereoisomers H 3 C Br H CH 2 CH 3 Br H 3 C H CH 2 CH 3 Consider Asymmetric Carbons 1. Prioritize groups using same rules as above (atomic number). 2. Orient molecule with lowest priority group back 3. Move from priority 1 to 2 to 3. Clockwise movement = R Counterclockwise movement = S ( )-2-bromobutane ( )-2-bromobutane CH 3 CH 2 CH 3 Br H CH 3 CH 2 CH 3 H Br
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3 C H CH 3 H 3 C H H H 3 C CH 3 H 3 C H O OH O OH Active analgesic and anti- inflammatory agent Inactive Ibuprofen (causes birth defects)
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6-StereochemistryHLSF07 - CHIRAL molecules: 1. Usually...

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