2-butanone, a ketone, is synthesized from 2-butanol as follow.
To prepare a solution P of acidified dichromate, a mass of hydrated sodium dichromate Na2Cr2O7.2H2O is dissolved in dilute sulfuric acid.
To prepare a solution Q of 2-butanol in ethyl ether, ½ mole of 2-butanol is dissolved in ethyl ether.
Solution Q is slowly added to solution P in a flask with stirring. The reaction that occurs is:
3CH3CHOHCH2CH3 + Cr2O72- + 8H+ --> 3CH3COCH2CH3 +2Cr3+ + 7H2O
The flask now contains 2-butanone, Na+, Cr3+, ethyl ether and water. To obtain the 2-butanone, the reaction mixture is poured from the flask into a separating funnel. The mixture will separate into two layers with the ether layer on top of the aqueous layer. The ether layer should contain most of the 2-butanone because the ketone is more soluble in ether than in water.
Sodium carbonate is added to the ether layer and some carbon dioxide is released. Anhydrous sodium sulfate is then added. As a result, a clear dry mixture of ether and the ketone is obtained. The sodium carbonate and sodium sulfate solids are filtered off.
(a)
Explain what color change would be seen.
(b)
Calculate the mass of 2-butanol that is dissolved in
ethyl ether.
(c)
Calculate the mass of hydrated sodium dichromate used.
(d)
If the actual yield is 30 g, what is the percentage
yield?
(e)
Describe how the 2-butanone is extracted from the aqueous
layer.
(f)
Why is (i) sodium carbonate (ii) anhydrous sodium
sulfate added?
(g)
Explain how 2-butanone and ethyl ether are separated.
After you have gone through some thought processes by attempting the question, watch this great video on how the experiment described in the question is done:
Organic Synthesis
Organic Synthesis
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