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Chapter 3 CONFORMATIONS OF ALKANES AND CYCLOALKANES

Chapter 3 CONFORMATIONS OF ALKANES AND CYCLOALKANES. Chapter 3: Conformations of Alkanes and Cycloalkanes. HEATS OF COMBUSTION AND RING STRAIN. Chapter 3: Conformations of Alkanes and Cycloalkanes. STRAIN ENERGY VS. RING SIZE. Chapter 3: Conformations of Alkanes and Cycloalkanes.

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Chapter 3 CONFORMATIONS OF ALKANES AND CYCLOALKANES

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  1. Chapter 3CONFORMATIONS OF ALKANES AND CYCLOALKANES Chapter 3: Conformations of Alkanes and Cycloalkanes

  2. HEATS OF COMBUSTION AND RING STRAIN Chapter 3: Conformations of Alkanes and Cycloalkanes

  3. STRAIN ENERGY VS. RING SIZE Chapter 3: Conformations of Alkanes and Cycloalkanes

  4. TYPES OF STRAIN IN ORGANIC MOLECULES (SUMMARY) • Torsional Strain: The strain due to eclipsing of bonds at neighboring carbon atoms. Energy cost – about 1 kcal/mol for C-H --- C-H eclipse, or 1.3 kcal/mol for C-H --- C-CH3 eclipse. • Steric Hindrance: The strain due to repulsive interactions, when atoms or groups approach each other too closely. Energy cost – about 0.8 kcal/mol for C-CH3 --- C-CH3 gauche interaction. • NOTE: The C-CH3 --- C-CH3 eclipsed interaction is a cumulative torsionalstrain + sterichindrance!!! • Angle Strain: The strain due to expansion or compression of bond angles. Energy cost – varies, depending on the actual bond angle. Chapter 3: Conformations of Alkanes and Cycloalkanes

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