Author: mostafa
•8:05 AM
Objective: Distinction between the three Dihydroxbenzene Isomers

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Chemicals:
catechol resorcinol

hydroquinone

FeCl3 · 6 H20

Solution of the dihydroxybenzenes: 0.625 g of catechol, resorcinol and hydroquinone, respectively, are dissolved in 20 mL of dist. water. The solutions should be colorless; if needed a "spatula-tip" full of charcoal is added. After shaking the suspension is filtered.
Ferric chloride solution: 1 g FeCl3 · 6 H20 are dissolved in 150 ml of dist. water.

Glass wares:
3 conical measures, graduated, 500 mL

3 glass stirring rods

beaker 200 mL

3 beakers 40 mL

3 snap-cap vials 20 mL

volumetric pipet 4 mL

volumetric pipet 10 mL

2 volumetric pipets 20 mL

1 pipette bulb

measuring cylinder 100 mL

Experimental procedure:

Three conical measures are set up as described in the following table.

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The individual dihydroxybenzene solutions are mixed with aqueous FeCl3. 4 mL of FeCl3 solution are poured into the first conical measure, 10 mL into the second measure and 20 mL into the third measure.
Results:
When treated with aqueous FeCl3, the aqueous dihydroxybenzene solutions will show the characteristic color change.


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Discussion:

Like phenol also catechol and resorcinol do form a colored complex with FeCl3.

Hydroquinone is oxidized rapidly to p-benzoquinone, which does not generate a colored complex with FeCl3.


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Redox equilibrium between hydroquinone and p-benzoquinone:


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Resorcinol shows no redox reaction with Fe3+. The two hydroxy groups in the meta position can not form a quinoid system. Thus a redox reaction between resorcinol and Fe3+ is impeded.

Catechol is only partially oxidized to o-benzoquinone.


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