Reaction with Alcohols Acetals and Ketals

Enzyme-catalyzed hydrolysis of amygdalin gives the carbohydrate gentiobiose along with benzaldehyde cyanohydrin, which dissociates to benzaldehyde and hydrogen cyanide. 

Depending on the amount of amygdalin present and the manner in which food is prepared from plants containing cyanogenic glycosides, toxic levels of hydrogen cyanide can result. 

Gynocardin is a naturally occurring cyanogenic glycoside having the structure shown. What cyanohydrin would you expect to be formed on hydrolysis of gynocardin, and to what ketone does this cyanohydrin correspond  

Many of the most interesting and useful reactions of aldehydes and ketones involve transformation of the initial product of nucleophilic addition to some other substance under the reaction conditions. An example is the acid-catalyzed addition of alcohols to aldehydes.The expected product, a hemiacetal, is not usually isolable, but reacts with an additional mole of the alcohol to give an acetal. 

When disturbed, many millipedes protect themselves by converting stored benzaldehyde cyanohydrin to hydrogen cyanide and benzaldehyde. 

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