The reaction of chlorine (Cl2) with 1,4-dimethylcyclohexane (show three possible monochlorination products) *what?!*

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asked by Cerise
  1. I think the tertiary carbons are most reactive followed by secondary then primary.

    posted by DrBob222
  2. I would start be defining which which 1,4-dimethylcyclohexane I was starting with, or considering a mixture of cis and trans?

    The tertiary carbons are most reactive as DrBob says, so there are two possible products from attack at the tertiary carbon:
    cis and trans 1-chloro-1,4-dimethyl cyclohexane.

    Attack at the secondary carbon adjacent to one of the methyl groups will result in 2-chloro-1,4-dimethylcyclohexane. If you start with a mixture of the cis and trans there are eight possible products which are:

    1R,2R,4R, 1-chloro-1,4-dimethyl cyclohexane.
    1S,2R,4R, 1-chloro-1,4-dimethyl cyclohexane.
    1R,2S,4R, 1-chloro-1,4-dimethyl cyclohexane.
    1R,2R,4S, 1-chloro-1,4-dimethyl cyclohexane.
    1R,2S,4S, 1-chloro-1,4-dimethyl cyclohexane.
    1S,2R,4S, 1-chloro-1,4-dimethyl cyclohexane.
    1S,2S,4R, 1-chloro-1,4-dimethyl cyclohexane.
    1S,2S,4S, 1-chloro-1,4-dimethyl cyclohexane.

    Attack at the primary carbon in one of the methyl groups will give
    1-chloromethyl-4-methylcyclohexane. Again you have the possibility of cis and trans depending on the starting material.

    posted by Dr Russ
  3. There is of course a deliberate mistake. I meant to list the eight as

    1R,2R,4R, 2-chloro-1,4-dimethyl cyclohexane


    posted by Dr Russ

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