Generalized Ranking of Electron Sources

Lone Pairs as Bronsted Bases Lone Pairs on Heteroatoms as Nucleophiles Softness, Solvation, Size, Basicity Easily Oxidizable Metals [Pg.151]

Organometallics Reactive If Large Electronegativity Difference, Metai Hydrides NaH and KH Are Bases, AIH4 and BH4 Are Good Nucleophiles [Pg.151]

Allylic Sources Ambident Nucleophiles Better Donors Increase Reactivity Vinylogous Allylic Sources Allyiic Alkyne Sources [Pg.151]

Alkenes Markovnikov s Rule Formation of the More Stable Carbocation Dienes Alkynes Allenes [Pg.151]

Poorer Electron Sources, Donors Activate, Electron-Withdrawing Groups Deactivate Donors Direct Electrophiles to the Ortho and Para Positions, Electron-Withdrawing Groups Direct Meta [Pg.151]