Identify the suitable reagent for the following conversion.

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Question

Identify the suitable reagent for the following conversion.

Accepted Answer

Correct Answer: C — (i) AlH(iBu)₂, (ii) H₂OStep-by-step Solution:The conversion is Ester → Aldehyde (partial reduction). This requires a selective reducing agent that stops at the aldehyde stage.A. H₂/Pd-BaSO₄ ✗: Lindlar's catalyst — reduces alkynes to cis-alkenes. Does not reduce esters.B. LiAlH₄ ✗: Too powerful and non-selective. Reduces esters all the way to primary alcohols (RCOOR' → RCH₂OH + R'OH). Cannot stop at aldehyde stage.C. DIBAL-H (AlH(iBu)₂) ✓: Diisobutylaluminium hydride. At −78°C, it reduces esters to aldehydes by delivering only one H⁻. The aluminium alkoxide intermediate is stable at low temperature and gives aldehyde on aqueous workup. RCOОР' + DIBAL-H (−78°C) → RCHOD. NaBH₄ ✗: Mild reducing agent — reduces aldehydes and ketones, but does NOT reduce esters under normal conditions.Key Concepts:DIBAL-H (Diisobutylaluminium hydride): Selective reducing agent for esters → aldehydes at low temperature (−78°C).LiAlH₄: Reduces esters → primary alcohols (over-reduction occurs).NaBH₄: Reduces only C=O (aldehydes, ketones); esters are inert.Reducing power order: LiAlH₄ > DIBAL-H > NaBH₄

Identify the suitable reagent for the following conversion.

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Identify the suitable reagent for the following conversion.

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More Questions from Aldehydes, Ketones and Carboxylic Acids

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