Single correct option
An optically active alcohol gives a yellow precipitate with . On acid-catalysed dehydration it gives three different alkenes (counting stereoisomers separately). The alcohol is
- A. Pentan-2-ol
- B. 3-Methylbutan-2-ol
- C. 2-Methylbutan-1-ol
- D. Pentan-3-ol
Show answer and solution
Answer: (A) Pentan-2-ol
The iodoform test needs , 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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