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Formula Sheets / Chemistry

Chapter 27

Aldehydes and Ketones

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Nucleophilic additionNamed reactionsPreparation

Nucleophilic addition

  • Reactivity

    HCHO>RCHO>RCOR′ (steric and electronic)
  • HCN, NaHSO3​, RMgX, NH2​–Z (oximes, hydrazones)

Named reactions

  • Aldol

    needs an α-H; dilute base⇒β-hydroxy carbonyl

  • Cannizzaro

    no α-H, conc. base: 2HCHO→HCOO−+CH3​OH

  • Reductions

    Clemmensen (Zn–Hg/HCl) and Wolff–Kishner (NH2​NH2​/KOH): C=O→CH2​

  • Tests

    Tollens (silver mirror) and Fehling (red ppt): aldehydes;iodoform: CH3​CO– and CH3​CH(OH)–

Preparation

  • Rosenmund: RCOClH2​, Pd/BaSO4​​RCHO;Stephen: RCN→RCHO;Etard: toluene→benzaldehyde
Alcohols Phenols and EthersCarboxylic Acids and Their Derivatives