Chapter 4 - 4.5 Conformations of Cyclohexane strain free...

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Sheet1 Page 1 Chapter 4: Organic Compounds: Cycloalkanes and Their Stereochemistry 4.1 Naming Cycloalkanes 4.2 Cis-Trans isomerism in Cycloalkanes no free rotation: these are stereoisomers (same connections, different 3D geometry) cis-same side, trans-opposite sides 4.3 Stability of Cycloalkanes: Ring Strain angle strain: bond angles are forced to deviate from the ideal 109 degree tetrahedral value however, large rings are unaffected and behave more like acyclic compounds. 4.4 Conformations of Cycloalkanes Cyclopropane: most strained- has bent bonds Cyclobutane: torsional strain- almost the same total strain as cyclopropane Cyclopentane: planar cyclopentane has no angle strain but lots of torsional strain- adopts a puckered conformation, increasing
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Unformatted text preview: 4.5 Conformations of Cyclohexane strain free chair conformation 4.6 Axial and Equatorial Bonds in Cyclohexane axial: perpendicular to the ring, equatorial: around the ring equator ring flips switch positions of functional groups 4.7 Conformations of Monosubstituted Cyclohexanes equatorial substituents are more stable than axial 1,3-diaxial interactions (sterics) 4.8 Conformations of Disubstituted Cyclohexanes Sheet1 Page 2 diequatorial is best larger substituent group is better in the equatorial position 4.9 Conformations of Polycyclic Molecules bridgehead carbons: shared carbons bridgehead hydrogens: bonded to shared carbons, determines if the ring is cis- or trans-fused cis-fused is more stable...
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This note was uploaded on 04/26/2009 for the course CHEM 227 taught by Professor Santander during the Fall '08 term at Texas A&M.

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Chapter 4 - 4.5 Conformations of Cyclohexane strain free...

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