Naturally occurring compounds called cyanogenic glycosides, such as lotaustralin, release hydrogen cyanide, IICN, when treated with aqueous acid. The reaction occurs by hydrolysis of the acetal linkage to form a cyanohydrin, which then expels HCN and gives a carbonyl compound.

(a) Show the mechanism of the acetal hydrolysis and the structure of the cyanohydrin those results.

(b) Propose a mechanism for the loss of HCN, and show the structure of the carbonyl compound thatforms.

Transcribed Image Text:

Cн-он Lotaustralin 0- но но- OH H3C CN