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.
The structure of the compound Q is
Match each of the compounds given in Column I with the reaction(s), that they can undergo, given in Column II.
| Column I | Column II | ||
|---|---|---|---|
| (A) |  |
(P) | Nucleophilic substitution |
| (B) |  |
(Q) | Elimination |
| (C) |  |
(R) | Nucleophilic addition |
| (D) |  |
(S) | Esterification with acetic anhydride |
| (T) | Dehydrogenation |
A carbonyl compound P, which gives positive iodoform test, undergoes reaction with MeMgBr followed by dehydration to give an olefin Q. Ozonolysis of Q leads to a dicarbonyl compound R, which undergoes intramolecular aldol reaction to give predominantly S.
The structure of the carbonyl compound P is
A carbonyl compound P, which gives positive iodoform test, undergoes reaction with MeMgBr followed by dehydration to give an olefin Q. Ozonolysis of Q leads to a dicarbonyl compound R, which undergoes intramolecular aldol reaction to give predominantly S.
The structures of the products Q and R, respectively, are
