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Question

An organic compound having structure as given below:
How many of the below given reactions will it give?
1. Ceric ammonium nitrate test
II. Brisk effervescence with sodium bicarbonate
III. Characteristic colouration with neutral ferric chloride after decarboxylation and reduction by Clemmenson's method
IV. Fehling's test
V. Tollen's test
VI. Orange dye with benzene diazonium chloride
VII. Molisch test

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Solution

I. Aliphatic alcohols gives ceric ammonium nitrate test. But the given molecule has phenolic OH group i.e. aromatic alcohol. Hence, it will not give ceric ammonium nitrate test.

II. The organic compound contains COOH group and hence it will give brisk effervescence (CO2) with NaHCO3.

III. The organic compound on decarboxylation gives CO2 and COOH group is removed. On Clemmensen reduction CHO group is reduced to CH3 group. And hence the final compound will only contain phenolic OH group which will react with neutral ferric chloride to give a deep violet colouration.

IV. The organic compound contains CHO group but it will not give Fehling's test because aromatic aldehydes (e.g. benzaldehyde) don't give Fehling's test.

V. The organic compound contains CHO group and hence it will give Tollen's test.

VI. Due to the presence of OH group, the organic compound undergoes coupling reaction with benzene diazonium chloride to form an orange dye.

VII. Molisch test is given by reducing carbohydrates and hence the organic compound will not give Molisch test.

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