An acyclic hydrocarbon P, having molecular formula C6H10, gave acetone as the only organic product through the following sequence of reactions, in which Q is an intermediate organic compound.
So, identify the possible structure of Q
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Solution
The final ozonolysis product indicates that the alkene before ozonolysis is
Also P(C6H10) has two degree of unsaturation and oxymercuration demercuration hydration indicates that it is an alkyne. As alkyne, on hydration, gives a carbonyl compound which on reduction with NaBH4 gives a 2o alcohol.
The secondory alcohol that can give above shown alkene on acid catalysed deydration is