A hydrocarbon (A) (molecular formula C_5H_(10)), on catalytic hydrogenation, produces 2-methylbutane. The compound (A) combines with HBr according to Markownikoff's rule to form the compound (B) which reacts with silver hydroxide to produce an alcohol (C ) having the molecular formula C_5H_(12)O. On oxidation, the alcohol(C ) yields a ketone (D). idenify A,B,C,D and give the reactions involved.

A hydrocarbon (A) (molecular formula C_5H_(10)), on catalytic hydrogen

1.	A hydrocarbon (A) (molecular formula C_5H_(10)), on catalytic hydrogenation, produces 2-methylbutane. The compound (A) combines with HBr according to Markownikoff's rule to form the compound (B) which reacts with silver hydroxide to produce an alcohol (C ) having the molecular formula C_5H_(12)O. On oxidation, the alcohol(C ) yields a ketone (D). idenify A,B,C,D and give the reactions involved.
Answer» Solution :The given changes are as follows: The molecular formula, `C_(5)H_(10)` is in AGREEMENT with the general formula of alkenes `(C_(n)H_(2n))` and on catalytic hydrogenation. (A) PRODUCES the SATURATED hydrocarbon, 2-methylbutane. THEREFORE, the compound (A) is an alkene. Now, the alcohol (C), on oxidation, produces the ketone (D). So, the alcohol must be a secondary `(2^(@))` alcohol. Again, this alcohol is obtained by the reaction of (B) with `AgOH`. So, (B) is a secondary bromide. `underset("2-bromo-3-methylbutane(B)")(CH_(3) - overset(overset(CH_(3))(\|))(C)H-overset(overset(Br)(\|))(C)H - CH_(3))` Now, (B) is produced by the reaction of (A) with HBr according to Markownikoff's. rule. So, the structure of (A) is: `CH_(3) - overset(overset(CH_(3))(\|))(C)H - CH = CH_(2)`[3-methylbut-1-ene(A)]