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JEE Advanced 2022 Paper 2 · Chemistry · Mole Concept and Stoichiometry · medium

10 mL of a gaseous hydrocarbon CxHy is exploded with 80 mL of O2 (excess) and the mixture is restored to the initial temperature and pressure, at…

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10 mL10\ \mathrm{mL} of a gaseous hydrocarbon CxHy\mathrm{C_xH_y} is exploded with 80 mL80\ \mathrm{mL} of O2\mathrm{O_2} (excess) and the mixture is restored to the initial temperature and pressure, at which water is liquid and its volume is negligible. The total volume decreases by 30 mL30\ \mathrm{mL}. Passing the residual gas through aqueous KOH\mathrm{KOH} decreases the volume by a further 40 mL40\ \mathrm{mL}. The number of open-chain (acyclic) isomers of this hydrocarbon, counting geometrical isomers separately, is _____.
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Answer: 4

For CxHy+(x+y4)O2→xCO2+y2H2O(l)\mathrm{C_xH_y}+(x+\tfrac y4)\mathrm{O_2}\to x\mathrm{CO_2}+\tfrac y2\mathrm{H_2O(l)}, the gas volume change per mole of hydrocarbon is a contraction of 1+y41+\tfrac y4 (liquid water occupies no volume, and excess O2\mathrm{O_2} cancels out). The KOH\mathrm{KOH} absorbs only CO2\mathrm{CO_2}: 10x=4010x=40, so x=4x=4. The first contraction gives 10(1+y4)=3010(1+\tfrac y4)=30, so y=8y=8. The hydrocarbon is C4H8\mathrm{C_4H_8} (check: 10 mL10\ \mathrm{mL} needs 60 mL60\ \mathrm{mL} O2\mathrm{O_2}, so 80 mL80\ \mathrm{mL} is indeed in excess). Open-chain isomers of C4H8\mathrm{C_4H_8} (one C=C): but-1-ene, (Z)(Z)-but-2-ene, (E)(E)-but-2-ene and 2-methylpropene. The cyclic isomers (cyclobutane, methylcyclopropane) are excluded.
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