The reagent diisobutylaluminum hydride (DIBALH) reduces esters to aldehydes. When nitriles are treated with DIBALH followed by mild acid hydrolysis, the product is also an aldehyde. Propose a mechanism for this reduction.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
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Chapter10: Alcohols
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Problem 10.39P: Dihydropyran is synthesized by treating tetrahydrofurfuryl alcohol with an arenesulfonic acid,...
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The reagent diisobutylaluminum hydride (DIBALH) reduces esters to aldehydes. When nitriles are treated with DIBALH followed by mild acid hydrolysis, the product is also an aldehyde. Propose a mechanism for this reduction.

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