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When 5-bromo-1-pentanol is treated with sodium hydride in diethyl ether, the product is analyzed to be...

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. Draw the mechanism of the first step of the reaction. Include ions in the answer. Include all lone pairs in your answer.

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O: Br NaH + NaBr+H2 5-bromo-1-pentanol Mechanism step-1 picking of hydroxy proton with H- NatH + H2Na+ Step 2 Br:

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