Answer to Question #1779 in Organic Chemistry for Ashley Schellenberg

Question

Mechanism of oxidation of benzaldoxime by Cl[sub]2[/sub] and NaOH.

Answer 1

treating NaOH and Cl₂(g) as NaOCl ,the mechanism should take place the following way:

PhCH=NOH + [OCl]- ----> HOCl + [PhCH=N-O]- <---> [PhCH-N=O]-

[PhCH-N=O]- + HOCl ----> PhCH(Cl)N=O + [OH]-

PhCH(Cl)N=O + [OH]- -----> H2O + [PhCClN=O]- <------> [PhC(Cl)=N-O]-

H2O + [PhC(Cl)=N-O]- ----> PhC(Cl)=N-OH + [OH]-

Thus, the overall reaction is:

PhCH=NOH + NaOCl ---> PhC(Cl)=N-OH + NaOH