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A hydrocarbon A (molecular formula, C5H10) yields 2-methyl butane on catalytic hydrogenation. A adds HBr (in accordance with Markownikoffs rule) to form a compound B which on reaction with silver hydroxide forms an alcohol C, C5H12O. Alcohol C, on oxidation gives a ketone D. Deduce the structures of A, B, C and D and show the reactions involved.

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(i) A adds HBr and its formula C5H10 suggests it to be an alkene. 

(ii) A on hydrogenation gives 2-methyl butane and thus, it has the chain of:

(iii) Addition of HBr on A gives B, which on treating with AgOH gives an alcohol C, which on oxidation gives a ketone D. Thus, C is secondary alcohol and B is secondary bromide which can be obtained only when A is 

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