Chapter4

Chapter4 - Why is this • In methylcyclohexane one is more...

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Chapter 4 - Cycloalkanes Names follow the same set of rules as linear alkanes. Alkane names are simply preceded by the word: CYCLO. General formula is C n H 2n . Stereoisomers – same connectivity but different spatial arrangement Ring Strain and torsional strain Ring sizes: Small rings – Cyclopropane, cyclobutane Common rings – Cyclopentane, cyclohexane Large rings – 13-membered and more 2
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Conformational Freedom To relieve strain rings can pucker and bend. Cyclopropane is not able to do this – See Newman projection. 3
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Conformational Freedom To relieve strain rings can pucker and bend. Cyclopropane is not able to do this – See Newman projection. 4
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Conformational Freedom To relieve strain rings can pucker and bend. Cyclopropane is not able to do this – See Newman projection. 5
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Substituted Cycloalkanes Axial and equatorial methylcyclohexanes are not equivalent in energy.
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Unformatted text preview: Why is this? • In methylcyclohexane, one is more stable than the other by 1.7 kcal/mol. 7 Substituted Cycloalkanes • Axial and equatorial methylcyclohexanes are not equivalent in energy. Why is this? • In methylcyclohexane, one is more stable than the other by 1.7 kcal/mol. 8 Competing for Equatorial Positions • Disubstituted cyclohexanes. 9 Fused or Bridged Ring Systems • Decalin 10 Fused or Bridged Ring Systems • Norbornane, norbornene… 11 Summary • Nomenclature • Ring sizes, Ring strain – Angle strain, torsional strain, steric strain • Conformational mobility, energy involved in transitions between conformations • Newman projections of chairs and boats • cis-, trans-, and axial, equatorial relationships • Fused ring systems. 12...
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This note was uploaded on 04/05/2012 for the course CHEM 140A taught by Professor Whiteshell during the Winter '04 term at UCSD.

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Chapter4 - Why is this • In methylcyclohexane one is more...

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