Organic Chemistry Alcohols, Phenols, Ethers and their Sulfur Analogs

Synthesis of Alcohols from Carbonyl Compounds

Topic overview

Start with the big picture

The lesson organizes alcohol synthesis from carbonyl compounds into hydride reductions, carbon–carbon bond-forming additions, and specialized or selective methods. It contrasts NaBH₄, LiAlH₄, and BH₃·THF by substrate scope and conditions, and introduces catalytic hydrogenation and the Meerwein–Ponndorf–Verley reduction. Grignard and organolithium reagents, acetylide additions, and selected other organometallic reactions show how carbonyl additions can produce different classes of alcohols. The topic also covers DIBAL-H, enantioselective reductions, and Prins and Peterson reactions. Together, these methods illustrate how reagent choice influences functional-group compatibility, product structure, and selectivity; the preview introduces the framework rather than replacing the full treatment of reaction mechanisms and methods.

Learning objectives

What you'll learn

  • Distinguish the substrate scope and conditions of common hydride reductions.
  • Predict alcohol class from Grignard addition to formaldehyde, aldehydes, and ketones.
  • Explain how organometallic additions form carbon–carbon bonds during alcohol synthesis.
  • Identify specialized approaches including DIBAL-H and enantioselective reductions.
  • Relate reagent choice to chemoselectivity and product structure.
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