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Answers
i) By the use of Felling's solution.
Propanal being an aldehyde reduces Fehling's solution to a red-brown precipitate of Cu2O, but propanone being a ketone does not.
ii) By using the Iodoform test.
Benzophenone does not contain any free methyl group so it will give a negative test. Benzophenone + Sodium Hypoiodite → No yellow ppt of CH₃.
iii) By warming with sodium hydrogen carbonate.
Benzoic acid gives effervescence hence producing CO2 gas while ethyl benzoate does not respond to this test.
iv) Iodoform test
To carry out a positive iodoform test, it is necessary to have a methyl ketone or methyl alcohol.
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(i) Propanal and propanone :
Propanal gives silver mirror test with Tollen's reagent. Propanone does not gives this test.
Propanal gives red ppt with Fehlings solution but propanone does not give this test.
(ii) Acetophenone and Benzophenone :
Acetophenone gives yellow ppt of idoform with alkaline solution of iodine (iodoform test) and Benzophenone doe not give this test.
(iii) Benzoic acid and Ethyl benzoate :
Ethyl benzoate does not react with sodium hydrogen carbonate and benzoic acid gives effervescence of carbon dioxide gas upon reaction with sodium hydrogen carbonate.
When ethyl benzoate is boiled with excess NaOH, it gives ethanol. Ethanol on heating with iodine gives yellow ppt of iodoform. This test is not given by benzoic acid.
(vi) Ethanal and Propanal :
Ethanal gives iodoform test but propanal does not give such test.