Fundamentals: Common Strong and Weak Nucleophiles

by Joe Ban Posted on November 30, 2011
@amoosari asks: is there an easier way to distinguish b/n strong nucleo/bases and weak ones?

Here are some common nucleophiles used in organic chemistry SN1, SN2, E1, and E2 reactions, sorted by strength:

  • VERY Good Nucleophiles: SH-, RS-, I-
  • Good Nucleophiles: CN-, N3-, Br-, HO-, RO-
  • Fair Nucleophiles: NH3, Cl-, F-, RCO2-
  • Weak nucleophiles: H20, ROH
  • VERY Weak Nucleophiles: RCO2H
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