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    Enantiomer of cis-1-chloro-3-methylcyclopentane

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    Draw the enantiomer of cis-1-chloro-3-methylcyclopentane which is R at C-1.

    1) What is the configuration of this molecule at C-3 (R and S)?

    2) When cis-1-chloro-3-methylcyclopentane and trans-1-chloro-3-methylcyclopentane are treated with sodium iodide in aqueous acetone, their rates of substitution are strikingly different. Explain clearly why this is so.

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    Solution Preview

    Please refer to the attached file. Cheers.
    a) Here, I drew the structure really big so that you can see the 3D picture better.

    Because at C-1, the configuration has to be R, Cl has to point upwards. (I showed the priority at C-1, with Cl the first, the carbon at position 2 the second. That way, going from 1 23, the rotation is clockwise. ...

    Solution Summary

    Solution shows how to draw molecule at C-3 as well as explaining why this and another molecule differ in substitution rates after a treatment with sodium iodide and aqueous acetone.