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    Explaining Regioselectivity of a Reaction

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    a) Briefly explain why each of the transformations below proceed as shown by providing a detailed reaction mechanism. As part of your answer, and where appropriate, include resonance structures in order to explain the regioselectivity of reaction. See attachment for structures

    b) Write a detailed reaction mechanism for the Fischer synthesis of 3-methylindole from the hydrazone formed from reaction of phenylhydrazine and acetone under acidic reaction conditions.

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    Solution Summary

    The regioselectivity of aromatics is explained using aromatic examples. Also included is the mechanism for a Fischer synthesis of 3-methylindole.