Question

When 5-bromo-1-pentanol is treated with sodium hydride in diethyl ether, the product is analyzed to be c5h10o. propose a likely structure for this product, suggesting a reasonable mechanistic pathway for its formation.?

Answer 1

The alcohol is likely to be first deprotonated by the strong base, generating an alkoxide ion, which can then undergo intramolecular SN2 reaction to afford the observed product, a cyclic ether. Cl .. OH .. NaH H2 Cl .. + O : Na .. O NaCl

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