Chapter 4 - 12 Cyclohexane Conformations Substituted...

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Chapter 4: Organic Compounds: Cycloalkanes and their Stereochemistry Cyclic compounds commonly encountered cholesterol H H H HO
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Cycloalkane Structure Cycloalkanes: Cycloalkane general formula 2
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Cycloalkane Nomenclature Find the Number substituents - 3
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Cycloalkane Cis-Trans Isomerism Cycloalkanes Much less cycloalkane 4
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Isomerism wo different Two different 5 these two isomers
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Stereoisomerism Stereoisomers: compounds having the same atom connectivity 6
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Cycloalkane Stability: Ring Strain Rings larger than Cyclic molecules assume non-planar conformations to Larger rings have 7
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Cycloalkane Stability: Baeyer Strain Theory 1885: 8
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Strain Summary Angle strain - orsional strain Torsional strain - Steric strain - 9
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Cycloalkane Conformations - Cyclopropane 3-membered ring Symmetrical with Requires that All C-H bonds eclipsed 10
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Cycloalkane Conformations - Cyclobutane Less angle strain than One C atom about Ring bend 11
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Cycloalkane Conformations - Cyclopentane Planar cyclopentane would Non-planarity Four carbon atoms are in a plane
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Unformatted text preview: 12 Cyclohexane Conformations Substituted cyclohexane rings etrahedral ngles Tetrahedral angles 13 Drawing Cyclohexane 14 Axial & Equatorial Bonds in Cyclohexane Chair conformation Chair cyclohexane has 15 Drawing Axial & Equatorial Hydrogens 16 Cyclohexane Conformational Mobility 17 Conformations of Monosubstituted Cyclohexanes Cyclohexane ring Two conformations 18 1,3-Diaxial Interactions Difference between axial and equatorial conformers due to H atoms of axial CH 3 group 19 Conformational Analysis of Disubstituted Cyclohexanes Steric effects of both Two isomers of 1,2-dimethylcyclohexane exist Cis isomer: Both conformations 20 Trans isomer: Larger alkyl groups 21 Conformational Analysis of Decalin Decalin: two cyclohexane rings joined Two isomeric forms of decalin: Flips and rotations 22 H atoms at bridgehead carbons H atoms at bridgehead carbons 23...
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This note was uploaded on 05/09/2010 for the course CHEMISTRY 138 taught by Professor Dicks during the Spring '10 term at University of Toronto- Toronto.

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Chapter 4 - 12 Cyclohexane Conformations Substituted...

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