Mechanism Flow Diagram

Key Points from Diagram

• Step 1 (B): Nucleophile attacks from below or above the plane of the sp2 carbon. Rate depends on electrophilicity of C and nucleophilicity of Nu.
• Step 2 (C): Alkoxide intermediate — carbon is now sp3 (tetrahedral). The negative charge is on oxygen.
• Step 3 (D): Protonation — in aqueous conditions, water or dilute acid provides the proton.
• Product (E): Depends on the nucleophile — CN- gives cyanohydrin; H- (from NaBH4) gives alcohol; RMgX gives alcohol with new C-C bond; NH2OH gives oxime (addition-elimination variant).

Application Examples