4) The classic synthesis of hydroquinone consists of two steps: a) oxidation of aniline with manganese dioxide in aqueous acid (HCI) to afford p-benzoquinone and b) reduction of the thus-produced quinone with iron powder in water (acid solution) to give hydroquinone. Formulate the respective (balanced) half reactions for the oxidation of aniline with MnO2 and the reduction of the pertinent quinone with Fe powder, respectively. On either side of the half reactions, indicate the oxidation state(s) of the element(s) that is (are) oxidized or reduced, respectively. Assume that the oxidation produces inorganic chlorides as byproducts whereas the reduction affords iron(II) oxide as waste and give a qualitative assessment of the atom-efficiency of this way of producing hydroquinone. Hints: Manganese ends up in the +2 oxidation state and the amino group is converted into an ammonium cation.
4) The classic synthesis of hydroquinone consists of two steps: a) oxidation of aniline with manganese dioxide in aqueous acid (HCI) to afford p-benzoquinone and b) reduction of the thus-produced quinone with iron powder in water (acid solution) to give hydroquinone. Formulate the respective (balanced) half reactions for the oxidation of aniline with MnO2 and the reduction of the pertinent quinone with Fe powder, respectively. On either side of the half reactions, indicate the oxidation state(s) of the element(s) that is (are) oxidized or reduced, respectively. Assume that the oxidation produces inorganic chlorides as byproducts whereas the reduction affords iron(II) oxide as waste and give a qualitative assessment of the atom-efficiency of this way of producing hydroquinone. Hints: Manganese ends up in the +2 oxidation state and the amino group is converted into an ammonium cation.
Chemistry
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Chapter1: Chemical Foundations
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Transcribed Image Text:4) The classic synthesis of hydroquinone consists of two steps:
a) oxidation of aniline with manganese dioxide in aqueous acid (HCI) to afford p-benzoquinone
and
b) reduction of the thus-produced quinone with iron powder in water (acid solution) to give
hydroquinone.
Formulate the respective (balanced) half reactions for the oxidation of aniline with MnO2 and the
reduction of the pertinent quinone with Fe powder, respectively. On either side of the half reactions,
indicate the oxidation state(s) of the element(s) that is (are) oxidized or reduced, respectively. Assume
that the oxidation produces inorganic chlorides as byproducts whereas the reduction affords iron(II)
oxide as waste and give a qualitative assessment of the atom-efficiency of this way of producing
hydroquinone.
Hints: Manganese ends up in the +2 oxidation state and the amino group is converted into an
ammonium cation.
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