Organic Chemistry

Learn the toughest concepts covered in Organic Chemistry with step-by-step video tutorials and practice problems by world-class tutors.

24. Carbohydrates

Monosaccharides - Kiliani-Fischer

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We know that aldose aldehydes are susceptible to the same nucleophilic addition reactions that we learned in carbonyl chemistry. Let's now learn a reaction that involves the formation of a cyanohydrin. The neat thing about this reaction is that the cyano group can then be reduced and hydrolyzed to form a new, chain-lengthened aldehyde.

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The original Kiliani-Fischer synthesis required two additional steps after cyanohydrin addition, and resulted in poor yields. However, an improved reducing agent, (H2, Pd/BaSO4), was developed to form imines instead of amines.

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Ready for a practice problem?

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Problem

Predict the product(s) for the following reaction. Provide the mechanism of the imine hydrolysis step if required.