Question

For a Schiff’s base condensation reaction using copper (II) acetate, salicaldehyde in methanol along with methylamine (5.2 ml, 33% in ethanol) with sodium acetate. Will the product still form if the solution has a pH of 1?

Answer 1

Schiff’s base reaction involves the nucleophilic attack by the N atom of the methyl amine on the carbonyl group of salicaldehyde. A pH of 1 is highly acidic and denotes the presence of protons (H⁺) in the solution. Under acidic conditions, methyl amine (CH₃NH₂) will be protonated by donating the lone electron pair over N to proton. Consequently, the nucleophilicity of methyl amine is significantly reduced and methyl amine can no longer attack the carbonyl group to produce the Schiff’s base.