Wohl Degradation

The ability to shorten (degrade) an aldose chain by one carbon was an important tool in the structure elucidation of carbohydrates. This was commonly accomplished by the Ruff procedure. An interesting alternative technique, known as the Wohl degradation has also been used. The following equation illustrates the application of this procedure to the aldopentose, arabinose. Based on your knowledge of carbonyl chemistry, and considering that the Wohl degradation is in essence the reverse of the Kiliani-Fischer synthesis.