When an ester, such as methyl propanoate ( ), is treated with exactly one equivalent of DIBAL-H at e — Redox Reactions and Volumetric Analysis Chemistry Question
Question
When an ester, such as methyl propanoate ( $CH_3CH_2COOCH_3$ ), is treated with exactly one equivalent of DIBAL-H at extremely low temperatures (-78 C) followed immediately by mild acidic hydrolysis, what is the primary organic product isolated?
Answer: B
💡 Solution & Explanation
Diisobutylaluminum hydride (DIBAL-H) at -78 C is a specialized, bulky hydride donor. It reduces esters to an intermediate tetrahedral aluminate complex that is stable at low temperatures. Upon aqueous workup, this collapses to yield an aldehyde (Propanal), stopping the reaction from over-reducing to an alcohol.
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