Fundamentals of Organic ChemistryChemistryBiomolecules
The cyclic hemiacetal shown below is in equilibrium with an acyclic open-chain compound X in aqueous solution. Identify the structure of compound X .
Correct answer
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Step-by-step solution
The given compound is a six-membered cyclic hemiacetal. In aqueous solution, it undergoes ring opening to form an acyclic aldehyde. The anomeric carbon ( C ₁ ), which is bonded to both the ring oxygen and a hydroxyl group, becomes the aldehyde carbonyl carbon ( - CHO ) upon ring opening. The ring oxygen is attached to C ₅ of the chain. When the C ₁- O bond breaks, this oxygen becomes a hydroxyl group ( - OH ) on C ₅ . The substituent on C ₅ is a - CH ₂ OH group, which constitutes C ₆ . Therefore, the open-chain for