Solvolysis and Hydrolysis

Unit 3 Macro Displacement

Solvolysis and Hydrolysis

Juan Juan
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IMFs involved: Hydrogen bonding, ion–dipole, hydrophobic

Why common: Hydrolysis is one of the most widespread reactions in nature and industry (proteins, esters, amides, ATP, environmental degradation). Solvolysis is the solvent-acting-as-nucleophile analog.

Examples:

  • Ester hydrolysis (acid or base catalyzed): RCOOR′ + H₂O → RCOOH + R′OH
  • Amide/peptide hydrolysis (proteases, acid/base)
  • ATP hydrolysis (enzyme-catalyzed; H-bonding in active site)
  • S_N1 solvolysis in water/alcohol
  • Glycosidic bond hydrolysis (carbohydrates)
  • Environmental hydrolysis of pesticides/plastics

Role of IMFs: Water H-bonding activates the carbonyl; ion–dipole solvation stabilizes the tetrahedral intermediate; hydrophobic pockets in enzymes position the substrate.

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