chapter 5

chapter 5 - Chapter 5 - 1 Chapter 5. Stereochemistry:...

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Chapter 5 - 1 Chapter 5. Stereochemistry: Chiral Molecules Stereoisomers: Isomers that have the same connectivity But that differ in the arrangement of their atoms in space ----> 3-dimensional appearances are different.
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Chapter 5 - 2 Enantiomers: Stereoisomers that are not superposable mirror images of each other. Superimposable Not superposable You can say Molecules are chiral <----> achiral.
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Chapter 5 - 3 To be chiral, a compound should have at least one atom bearing different groups or atoms. How? 1. Two identical groups. 2. Plane of symmetry ---> means achiral Stereocenter or stereogenic center or chirality center H 3 C CH 3 HO H Question) Stereogenic? Ans) No. H Br Cl Me away from me (or down) towards me (or up) Question) Stereogenic? Ans) Yes. H 3 C CH 3 H OH
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Chapter 5 - 4 Plane of symmetry 2-chloropropane: symmetry of plane ---> achiral 2-chlorobutane: no symmetry of plane ---> chiral 5.7. (R-S) System - CIP system (Cahn-Ingold-Prelog) Stereocenter -----> ( R ) conFguration or ( S ) conFguration How to assign the stereochemistry: Look at the stereogenic center.
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Chapter 5 - 5 1. Assign the priority. - The higher atomic number, the higher priority. HO C H 2 H 3 C H CH 3 1 4 2 (or 3) 2 (or 3) ( R )-2-butanol or ( S )-2-butanol - Assign the priorities at the frst point oF diFFerence HO C H 2 H 3 C H CH 3 1 4 3 2 C H H H C H H C H H H the same the same H is lower than C in priority.
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This note was uploaded on 10/22/2010 for the course CHEM 322A at USC.

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chapter 5 - Chapter 5 - 1 Chapter 5. Stereochemistry:...

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