org13
Oxidation of primary, secondary and tertiary butanoles


* Sulfuric acid is very corrosive, * Chromium compounds are poisonous. *Experiemnt for a chemistry teacher. * Use atray.  * Do not forget your goggles!
During oxidation of ethanol (methylated spirit) with acidic potassium dichromate solution each ethanol molecule splitted off two H-atoms resulting in the formation of  ethanal.
In the following experiment you will take primary, secondary and tertiary butanol to learn about isomerism.
What you need:TDropper bottles with  primary, secondary, tertiary butanole, concentrated sulfuric acid, diluted potassium dichromate solution, three small injection bottles.
Experiment:* Take the three bottles to mix one drop of each of the butanol samples with 3 drops of the potassium dichromate solution.  * Add 1 drop of concentrated sulfuric acid to each of the samples and mix.
Observation Right photo:
The orange colour of dichromate ions only disappears in the samples of primary and secondary butanol. It is replaced by the blueish colour of chromium ions.
Explanation: Molecules of primary and secondary alcohols are electron donors in direct redox reactions, dichromate ions are electron acceptors. The blueish colour indicates chromium ions (Cr3+(aq)).

Primary butanol (aldehyde is formed) :
3 CH3(CH2)2CH2OH(l) + Cr2O72-(aq) + 8 H+(aq) ---> 3 CH3(CH2)2CHO(l) + 2 Cr3+(aq) + 7 H20(l)
Secondary butanol (ketone is formed):
3 CH3CH2CHOHCH3(l) + Cr2O72-(aq) + 8 H+(aq) ---> 3 CH3CH2COCH3(l) + 2 Cr3+(aq) + 7 H20(l)
Tertiary butanol (no oxidation):
3 (CH)3COH(l) + Cr2O72-(aq) + 8 H+(aq) --->|| no reaction, no H atoms at C with OH-group

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