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An organic compound (A) of molecular formula C3H6O reduces Tollen’s reagent on reaction with methyl magnesium bromide followed by acid hydrolysis gives (B) of formula C4H10O. (B) gives blue colour in victor meyer test. (B) on reaction with Cu at 573 K gives (C) of formula C4H8O (C) on reaction with hydrazine and sodium ethoxide gives (D) of molecular formula C4H10 . identify A,B,C,D and explain the reactions involved.

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1. An organic compound (A) reduces Tollen’s reagent it must be an aldehyde. From the formula, it is identified as CH3 – CH2 – CHO propanal.

2. Propanal on reaction with methyl magnesium bromide followed by acid hydrolysis gives (B) as Butan – 2 – ol. It must be a secondary alcohol and gives blue colour with victor meyer’s test. H

4. Wolf – Kishner reduction.

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