Sodium bisulfite adds reversibly to aldehydes and a few ketones to give bisulfite addition products.

(a) Write a curved-arrow mechanism for this addition reaction; assume water is the solvent.

(b) The reaction can be reversed by adding either H₃O⁺or ^–OH. Explain this observation using Le Châtelier’s principle and your knowledge of sodium bisulfite reactions from general or inorganic chemistry.

(c) Deduce the structure of the bisulfite addition product of 2-methylpentanal.

Transcribed Image Text:

:0: Na H-S-0:- :O: Figure P19.42 :0: Na S-OH + R-CH Im]. :0: :0: || sodium bisulfite :ÖH | R-CH o=s=0 :0:- Na+