cyclohexane-conformers

cyclohexane-conformers - Cyclohexane 1 Axial and Equatorial...

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Unformatted text preview: Cyclohexane 1 Axial and Equatorial Positions of Cyclohexane Pink - Axial Blue - Equatorial 2 H ring flip H H H H CH3 equatorial methyl H Cyclohexane Axial Positions More Crowded H H 1,3-diaxial interaction axial methyl CH3 H H 1.8 kcal/mol more stable conformation 3 axial Methyl Cyclohexane 4 equatorial Methyl Cyclohexane 5 CH3 cis-1,2-dimethylcyclohexane 1 2 CH3 CH3 trans-1,2-dimethylcyclohexane 1 2 CH3 2 H 2 ax CH3 1 H CH3 eq H ax CH3 1 H CH3 a x dimethylcyclohexane H eq 1 CH3 2 CH eq 3 H lower in energy ax CH3 ring flip eq 1 CH3 2 H H same interactions in both conformations -equal in energy ring flip different interactions in both conformations -- NOT equal in energy 6 cis-1,2-dimethylcyclohexane 7 cis-1,2-dimethylcyclohexane 8 trans-1,2-dimethylcyclohexane 9 trans-1,2-dimethylcyclohexane 10 trans-1,2-dimethylcyclohexane 11 1 CH3 cis-1,3-dimethylcyclohexane 3 CH3 1 CH3 3 H 3 CH3 ax H eq H3C trans-1,3-dimethylcyclohexane 3 CH3 ring flip H 3 H 1 CH3 1 CH3 eq eq lower in energy H 3 H eq H3C cis-1,3-dimethylcyclohexane ax CH3 1 H ring flip different interactions in both conformations -- NOT equal in energy ax CH3 1 H ax CH3 same interactions in both conformations -equal in energy 12 cis-1,3-dimethylcyclohexane 13 H3C H3C 1 CH3 H3C eq cis-1,4-dimethylcyclohexane 4 1 CH3 H H trans-1,4-dimethylcyclohexane 4 4 4 ax CH3 ax CH3 1 H 4 ax CH 3 H 1 CH3 H 4 1 CH3 H eq eq 1,4-dimethylcyclohexane ring flip ring flip eq H3C lower in energy same interactions in both conformations -- H equal in energy ax CH3 1 H different interactions in both conformations -- NOT equal in energy 14 CH 4 H3C ax CH3 CH 1 H ax CH 3 4 1 CH eq CH3 CH3 1,4-dimethylcyclohexane ring flip H kcal/mol strain CH3 Y 0.9 H kcal/mol strain - CH3 0.95 1 lower in energy 0.12 -CH2CH3 1.1 4 H3C eq cis-1-isopropyl-4-methylcyclohexane CH3 H3C H Y The larger group would prefer to be in the equatorial position -NOT equal in energy -F 0.25 -CH(CH3)2 2.7 Y - Cl 0.25 -C(CH3)3 H -Br 0.5 1,3-diaxial interaction -OH 15 H H boat cyclohexane H H H H H Boat Conformations H norbornane 16 ...
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This note was uploaded on 12/22/2011 for the course CHEM 3053 taught by Professor Laurashirtcliff during the Fall '11 term at Oklahoma State.

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cyclohexane-conformers - Cyclohexane 1 Axial and Equatorial...

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