SOCl₂: Converting Alcohols to Alkyl Chlorides (Mechanism + Stereochemistry)

Learn how SOCl2 converts alcohols to alkyl chlorides. Chlorosulfite intermediate, role of pyridine, inversion vs retention, and common pitfalls.

  • Reaction: ROH → RCl (SOCl2)
  • What it does: Replaces –OH with –Cl
  • Typical reagents: SOCl2 ± pyridine
  • Key intermediate: Chlorosulfite ester (ROSOCl)
  • Driving force: Formation of SO2(g) + HCl(g)
  • Exam type: Stereochemistry
  • Exam type: Choose mechanism
  • Exam type: Reagent selection

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