Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: beardy on November 27, 2015, 06:59:34 PM

Title: Wohl Degradation Reagent Inquiry
Post by: beardy on November 27, 2015, 06:59:34 PM

In Wohl degradation, one carbon is removed from a carbohydrate chain.
The following sequential reagents are mentioned:

1) NH₂OH
2) acetic anhydride
3) NaOMe

Would acid chloride be an appropriate substitute for step 2? My reasoning is that acid chlorides are more reactive than acetic anhydrides and should therefore work.

Title: Re: Wohl Degradation Reagent Inquiry
Post by: phth on November 30, 2015, 05:27:03 AM

Acid chlorides are more reactive, but acetic anhydride is easier to handle.  The time of the reaction will vary.

Title: Re: Wohl Degradation Reagent Inquiry
Post by: Dan on November 30, 2015, 07:14:26 AM

The presence of acetate may speed up the nitrile formation step, depending on what the RDS is. If you use an acid chloride, the acetylation will be faster, but the elimination of acetic acid the will be slower.

Title: Re: Wohl Degradation Reagent Inquiry
Post by: beardy on December 01, 2015, 02:04:18 AM

Thanks  ;D