Chapter 16 with notes - Chapter 16 Conformational analysis...

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Chapter 16 – Conformational analysis Instructor: Dr. Daniel Seidel Chem 315 Different conformers of a molecule result by rotation around single bonds.
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three compounds, each shown in two conformations three pairs of stereoisomers: each member of a pair has a different configuration It is important to distinguish conformation from configuration Rotational barriers H H H H H H O N H Me Me 12 kJ/mol 30 kJ/mol 85 kJ/mol 260 kJ/mol
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Conformations of ethane
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Conformations of ethane: The Newman projection staggered eclipsed
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Torsional energy profile of ethane
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What is the origin of the rotational barrier in ethane? Van der Waals radii of vicinal hydrogens do not overlap in ethane The rotational barrier in propane is 14 kJ/mol
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Torsional energy profile of butane
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Ring Strain Note that the red line indicates the hypothetical ring strain if the ring was planar. The green line represents actual experimental data. Note that the enthalpy of combustion per CH2 group is very similar for all linear alkanes.
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Saturated rings with more than 3 carbons are not planar Conformations of cyclohexane Cyclopropane
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Cyclobutane
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