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Homework Help: Bromination and Nitration

  1. Jun 8, 2007 #1
    1. The problem statement, all variables and given/known data
    1) What other nitration products in a electrophilic nitration of benzoic acid would be formed if each reaction were carried out at a higher temperature?

    2) The nitration of hydroquinone leads to a low yield of nitrohydroquinone. Propose the structure of the major product: HINT: nitric acid can also function as an oxidizing agent.

    2. Relevant equations
    3. The attempt at a solution

    Please correct me if I am wrong.
    For #1: I think since it is at higher temperature, and benzoic acid is a meta director, the both meta position of the benzene ring will have NO2 attached to it so it will be a 3,5 - dinitro product.

    For #2: I was thinking the structure of hydroquinone is [PLAIN]http://en.wikipedia.org/wiki/Image:Hydroquinone.svg.[/URL] [Broken] Since it has two hydroxide attached and they are all ortho/para director, i think the NO2 will be attached to all four remaining positions.

    Can someone please help me out? Thanks.
    Last edited by a moderator: May 2, 2017
  2. jcsd
  3. Jun 11, 2007 #2


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    The hint said that nitric acid can also act as an oxidant. How might you use this hint?
    Last edited by a moderator: May 2, 2017
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