CHAPTER 5 NOTES

CHAPTER 5 NOTES - CHAPTER 5 STEREOCHEMISTRY - - ISOMERISM -...

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CHAPTER 5 STEREOCHEMISTRY - - ISOMERISM - - NOMENCLATURE: ( R – S ) SYSTEM - - OPTICAL ACTIVITY: ( d , l ) DESIGNATIONS - - FISCHER PROJECTION FORMULAS - - CYCLIC COMPOUNDS - - ENANTIOMER RESOLUTION - - STEREOCENTERS OTHER THAN C - - CHIRALITY DUE TO OVERALL ASYMMETRY ( - NOT DUE TO C ATTACHED TO 4 DIFFERENT GROUPS )
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ISOMERISM - - SEE CLASSIFICATION SCHEME p. 196 - - CHIRAL MOLECULES - - NON-SUPERPOSABLE UPON THEIR MIRROR IMAGES e.g. RIGHT HAND v. LEFT HAND RIGHT EAR v. LEFT EAR - - HAVE NO PLANES OF SYMMETRY e.g.: cf. C H 4 ; C H 3 Cl ; C H 2 Cl Br ; C H Cl Br I - - WHICH HAVE A PLANE OF SYMMETRY ? - - WHICH DO NOT ? - - SO ? - - WHICH IS (ARE) CHIRAL ? - - TYPICALLY : FOR CHIRAL MOLECULES - - EXIST AS A PAIR OF ENANTIOMERS - - INTERCONVERSION RARE - WHY ? - - BIOLOGICAL IMPORTANCE - - READ SECTION 5.3 , 5.4
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NOMENCLATURE:
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( R – S ) SYSTEM e.g. “ HAND ” : RIGHT / LEFT - - NEED TO SPECIFY ! ( SO AS TO BE AN UNAMBIGUOUS DESCRIPTION ) - - CAHN INGOLD PRELOG RULES: - - ASSIGN PRIORITY ORDER TO THE 4 GROUPS AT THE STEREOCENTER ( 1 , 2 , 3 , 4 ) LOWEST PRIORITY GROUP - - VIEW MOLECULE SO THAT: GROUP 4 IS DIRECTED AWAY FROM YOU - - TRACE PATH : ( 1 à 2 à 3 ) - - EXAMINE DIRECTION OF PATH CLOCKWISE : “ R COUNTERCLOCKWISE : S
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- - DO PROBLEMS: 5.9 , 5.11 , 5.12 p. 205 – 206 OPTICAL ACTIVITY - - ENANTIOMERS HAVE SAME M.P. B.P.
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This note was uploaded on 04/14/2008 for the course CHEM 2370 taught by Professor Dandekar during the Fall '07 term at North Texas.

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CHAPTER 5 NOTES - CHAPTER 5 STEREOCHEMISTRY - - ISOMERISM -...

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