An organic compound P with molecular formula C9H18O2 decolorizes bromine water and also shows positive iodoform test. P on ozonolysis followed by treatment with H2O2 gives Q and R. While compound Q shows positive iodoform test, compound R does not give positive iodoform test. Q and R on oxidation with pyridinium chlorochromate (PCC) followed by heating give S and T, respectively. Both S and T show positive iodoform test.
Complete copolymerization of 500 moles of Q and 500 moles of R gives one mole of a single acyclic copolymer U. [Given, atomic mass : H=1,C=12,O=16 ]
Sum of number of oxygen atoms in S and T is ____.
Answer: 2
Solution
From the given information:
P has formula C9H18O2, decolorizes Br2 (unsaturation), and gives positive iodoform test (CH3CO− or CH3CH(OH)−).
Ozonolysis gives Q and R, where Q gives iodoform test but R does not.
PCC oxidation followed by heating converts Q → S and R → T, both giving iodoform test.
P is likely a β-hydroxy unsaturated ester. Ozonolysis gives:
