Lect14_0923 - Ch. 4 - 1 10. The Relative Stabilities of...

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Ch. 4 - 1
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Ch. 4 - 2 10. The Relative Stabilities of Cycloalkanes: Ring Strain Cycloalkanes do not have the same relative stability due to ring strain Ring strain comprises: Angle strain –resu lt ±of±dev iat ion ±from± ideal bond angles caused by inherent structural constraints Torsional strain – result of dispersion forces that cannot be relieved due to restricted conformational mobility
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Ch. 4 - 3 10A. 10A. Cyclopropane Cyclopropane 10B. 10B. Cyclobutane Cyclobutane 10C. 10C. Cyclopentane Cyclopentane
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Ch. 4 - 4 11. Conformations of Cyclohexane: The Chair & the Boat
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Ch. 4 - 5 12. Substituted Cyclohexanes: Axial & Equatorial Hydrogen Atoms Equatorial hydrogen atoms in chair form Axial hydrogen atoms in chair form
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Ch. 4 - 6 H G G H (equatorial G) (more stable) (axial G) (less stable) Substituted cyclohexane Two different chair forms H G H G
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Ch. 4 - 7 G G (equatorial) (axial) At 25 o C G % of Equatorial % of Axial F6 0 4 0 CH 3 95 5 i Pr 97 3 t Bu > 99.99 < 0.01
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Ch. 4 - 8 13. Disubstituted Cycloalkanes Cis-Trans Isomerism cis
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Lect14_0923 - Ch. 4 - 1 10. The Relative Stabilities of...

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