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JEE Main 2022 · Chemistry · Alcohols, Phenols, Ethers and Haloalkanes · medium

An optically active alcohol C5H12O gives a yellow precipitate with I2/NaOH. On acid-catalysed dehydration it gives three different alkenes (counting…

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An optically active alcohol C5H12O\mathrm{C_5H_{12}O} gives a yellow precipitate with I2/NaOH\mathrm{I_2/NaOH}. On acid-catalysed dehydration it gives three different alkenes (counting stereoisomers separately). The alcohol is
  1. A. Pentan-2-ol
  2. B. 3-Methylbutan-2-ol
  3. C. 2-Methylbutan-1-ol
  4. D. Pentan-3-ol
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Answer: (A) Pentan-2-ol

The iodoform test needs CH3CH(OH)−\mathrm{CH_3CH(OH)-}, which rules out 2-methylbutan-1-ol and pentan-3-ol (also achiral). Both pentan-2-ol and 3-methylbutan-2-ol are chiral with this group. Dehydration of pentan-2-ol gives pent-1-ene, (E)-pent-2-ene and (Z)-pent-2-ene, i.e. three alkenes. 3-Methylbutan-2-ol gives only 3-methylbut-1-ene and 2-methylbut-2-ene (two). Hence the alcohol is pentan-2-ol.
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