lecture06_s05-1

lecture06_s05-1 - 5.12 Lecture 6 5.12 6 V. Alkanes VI....

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5.12 Lecture 6 5.12 Lecture 6 V. Alkanes VI. Stereochemistry H. Cyclohexane A. Classification ¸ The “Chair” B. Chirality 2. Ring Flipping C. Optical Activity 3. Monosubstituted D. Chirality at Other Atoms 4. Disubstituted E. Prochirality I. Polycyclic systems Name That Molecule! Name That Molecule! 8- sec -butyl-3-ethyl-6-isopropyl-5,5,10-trimethyl-7-neohexyldodecane or sec -butyl- 7-(3,3-dimethylbutyl)-3-ethyl-6-(1-methylethyl)-5,5,10-trimethyldodecane 1
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VI. Stereochemistry VI. Stereochemistry A. Classification of Stereoisomers B. Chirality 1. Conformational 1. Definition a. Bond rotation 2. Determining chirality b. Ring flip 3. Origins of chirality c. Nitrogen inversion a. Carbon with 4 diff. subst. 2. Configurational b. Axial chirality a. Cis-trans c. Meso compounds b. 4 different subst. on carbon 4. Facts about Chirality c. Subclasses of a) and b) C. Optical Activity i. Enantiomers D. Chirality at Other Atoms ii. Diastereomers E. Prochirality Classifying Classifying Stereoisomers Stereoisomers Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski. 2
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Classifiying Stereoisomers Classifiying Stereoisomers : Example 1 : Example 1 Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski. Classifying Classifying Stereoisomers Stereoisomers : Example 2 : Example 2 Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski. 3
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Classifying Classifying Stereoisomers Stereoisomers : Example 3 : Example 3 Courtesy of Jeffrey S. Moore, Department of Chemistry, University of Illinois at Urbana-Champaign. Used with permission. Adapted by Kimberly Berkowski. Prioritize Using Prioritize Using Cahn -Ingold Ingold -Prelog Prelog Rules Rules 1. Look at atoms directly attached to chirality center a) higher atomic number = higher priority b) heavier isotopes = higher priority 2. If no difference at first attached atom, move along the chain until
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lecture06_s05-1 - 5.12 Lecture 6 5.12 6 V. Alkanes VI....

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