Question 14
Characterization and Copolymerization of Organic Compound P
An organic compound with molecular formula decolorizes bromine water and also shows positive iodoform test. on ozonolysis followed by treatment with gives and . While compound shows positive iodoform test, compound does not give positive iodoform test. and on oxidation with pyridinium chlorochromate (PCC) followed by heating give and , respectively. Both and show positive iodoform test. Complete copolymerization of 500 moles of and 500 moles of gives one mole of a single acyclic copolymer . [Given, atomic mass: , , ]
Sum of number of oxygen atoms in and is _____.
Detailed Solution
- Compound () is an alkene that contains hydroxy groups because its oxidative ozonolysis yields hydroxy acids and .
- Based on the tests, is 3-hydroxybutanoic acid () and is 3-hydroxypentanoic acid ().
- gives a positive iodoform test due to the group, while does not.
- Oxidation of with gives acetoacetic acid (), which on heating undergoes decarboxylation to give acetone (, ).
- Oxidation of with gives 3-ketopentanoic acid (), which on heating undergoes decarboxylation to give 2-butanone (, ).
- (acetone) has 1 oxygen atom and (2-butanone) has 1 oxygen atom.
- Sum of oxygen atoms = .
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