Ch_322a_4.016

Ch_322a_4.016 - Substituted Cyclohexanes In the chair...

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Substituted Cyclohexanes In the chair conformation of cyclohexane, there are axial and equatorial positions that interchange during chair-chair interconversion. For simple cyclohexane, the two chair conformations are identical . H H H H H H H H H H H H H H H H H H H H H H H H fast Stereoisomeric Forms of Monosubstituted Cyclohexanes In monosubstituted cyclohexanes , the substituent may be either in an equatorial or axial position which are different stereoisomers .
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Example: Methylcyclohexane axial- methylcyclohexane chair-chair interconversion equatorial -methylcyclohexane H H H H H H H H H H H CH 3 H H H H H H H H H H H CH 3 fast fast The axial- and equatorial -methylcyclohexane are stereoisomers. The equatorial isomer is more stable by 1.8 kcal/mol and therefore dominates in the fast equilibrium. Why is equatorial-methylcyclohexane more stable?
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Relative Stabilities of the Methylcyclohexanes The stability difference between the equatorial and axial
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Ch_322a_4.016 - Substituted Cyclohexanes In the chair...

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