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JEE Advanced levelSingle correct optionDifficulty 3 of 3o1206

5-Hydroxypentanoic acid is warmed with a trace of under high dilution. The main product is

  1. Aoxolan-2-one
  2. Boxepan-2-one
  3. C5-hydroxypentanal
  4. Doxan-2-one

Answer: D

Intramolecular Fischer esterification: the OH at C-5 attacks the protonated carboxyl carbon. The ring contains O, C5, C4, C3, C2 and C1 i.e. six atoms, giving the delta-lactone oxan-2-one (loss of water). Oxolan-2-one would come from the 4-hydroxy acid.
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