Conversion of Alcohol via SOCl2-SN2

• Primary and Secondary Alcohols Only

• Net Reaction

  • R-OH + SOCl2 ---> R-Cl + SO2 + HCl

• Reaction Mechanism

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Reaction Mechanism

1. R-OH + Cl-S-Cl ---> R-O+-S-Cl + Cl -

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O H O

2. R-O+-S-Cl + Cl- ---> R-Cl + HSO2Cl

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H O

3. HSO2Cl ----> H-Cl(g) + SO2(g)

Transp 139-Mechanism