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    Mononitration Products

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    Predict the most likekly mononitration product from each of the following compounds. Explain the reasons.

    a) benzotriflouride
    b) 4-ethyl toluene
    c) 1,3-dimethyl-5-nitrobenzene
    d) Br-C6H4-COOCH2CH3 (1bromobenze 3-ethyl acetate)

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    Solution Preview

    There are a number of substituents to consider here:
    fluoro, methyl, ethyl, nitro, bromo, ester.

    They can be classed into groups, accoridng to their directing effect on nitration:

    Halo- groups direct nitration to positions 4, 2 and 3 (in that order) and tend to deactivate the nitration process.

    Alkyl groups also direct nitration to positions 4, 2 and then 3 but this is because they activate the nitration process.

    Ester and nitro groups direct to 3 and then 2 and 4 by deactivating.

    This last group is ...

    Solution Summary

    The solution contains guidance on how to go about predicting the most likely mononitration products from a series of specified compounds including benzotriflouride, 1,3-dimethyl-5-nitrobenzene and others.