Question

1. A hydrocarbon (A) with molecular formula, C₅H₁₀, yields 2-methylbutane on catalytic hydrogenation.
2. A adds HBr (in absence of peroxide) to form a compound B.
3. B on reaction with silver hydroxide forms an alcohol C, C₅H₁₂O.
4. Alcohol (C) on oxidation gives a ketone D. 

Deduce the structure of A, B, C and D giving the proper explanation for it.

chem XI Q13

Answer 1

(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:

\(C - C - \underset{CH_3}{\underset |C} - C\)

(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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