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Decalin is an example of fused bicyclic ...

Decalin is an example of fused bicyclic systems where two six membered rings share common C-C bond. There are two possible arrangements : trans and cis-decalin.

(i) Draw cis and trans decalin using the chair form for these species
(ii) Which isomer is more stable? Give explanation.

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Knowledge Check

  • Cyclonexane exists its two chair conformations in rapid equilrium at room temperature. Each carbon atom on a cyclohexane ring has one axial and one equatorial hydrogen. Ring-flipping converts axial II's to equatorial H's and vice-versa. In substituted cyclohexane, groups larger than hydrogen are more stable in the equatorial position. The cis isomer has two groups on the same side of the ring, either both up or both down. The trans isomer has two groups on opposite side of the ring one up and one down. Find out most stable conformer of cis-3-fluorocyclohexanol.

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    B
    C
    D

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    A
    B
    C
    D
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  • Cyclonexane exists its two chair conformations in rapid equilrium at room temperature. Each carbon atom on a cyclohexane ring has one axial and one equatorial hydrogen. Ring-flipping converts axial II's to equatorial H's and vice-versa. In substituted cyclohexane, groups larger than hydrogen are more stable in the equatorial position. The cis isomer has two groups on the same side of the ring, either both up or both down. The trans isomer has two groups on opposite side of the ring one up and one down. Find out most stable substituted cyclohexane among the following:

    A
    B
    C
    D