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An organic compound (A) of molecular formula C3H6 on reaction with Conc. H2SO4 and H2O gives ClH5O as (B) as a MarkownikoWs product. (B) on oxidation with Cu at 573 K gives (C) of formula C3H6O. (C) on reaction with CH3MgBr followed by acid hydrolysis yields (D) as C4H10O which will not give any colour in Victor Meyer’s test. Identify A, B, C, D and explain the reactions involved.

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1. An organic compound (A) is identified from the molecular formula as CH3 – CH = CH2 propene.

2. Propene on hydrolysis in acid medium, Markownikoff’s rule is followed and the product formed is

3. Propan – 2 – ol on reaction with Cu at 573 K undergoes dehydrogenation reaction to produce Propanone as (C).

4. Propanone on reaction with CH3MgBr followed by acid hydrolysis gives tertiary butyl alcohol (D). It will not give any colouration in Victor Meyer’s test.

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