JEE Advanced 2024 Paper 2 · Q15 · Alcohols, Phenols, Ethers
PARAGRAPH I: An organic compound P with molecular formula $C_9H_{18}O_2$ decolorizes bromine water and also shows positive iodoform test. P on ozonolysis followed by treatment with $H_2O_2$ 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]
The molecular weight of U is _____.
Reveal answer + step-by-step solution
Correct answer:93018
Solution
From the structures derived in the official solution, Q has molar mass 104 g/mol and R has molar mass 118 g/mol. Total mass of monomers before condensation = $500 \times 104 + 500 \times 118 = 52000 + 59000 = 111000$ g. Copolymerization between the hydroxy-acid monomers forms ester linkages, expelling one H$_2$O per linkage. To join 1000 monomers into one acyclic chain, 999 H$_2$O molecules are released. Mass of water expelled = $999 \times 18 = 17982$ g. Hence MW(U) = $111000 - 17982 = 93018$ g/mol.
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