tautomerism

Pyranoses and Furanoses: Ring-Chain Tautomerism In Sugars

Pyranoses and Furanoses: Ring-Chain Tautomerism In Sugars

July 13, 2017

The Many Forms Of Glucose What’s the structure of glucose? A simple question! but one with many “right” answers. The first question to ask, which we covered in our recent post on D- and L- sugars,…

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Hydroboration and Oxymercuration of Alkynes

Hydroboration and Oxymercuration of Alkynes

May 14, 2013

Alkyne chemistry bears many resemblances to alkene chemistry, but in these first few posts on the subject, the purpose is to illustrate how one seemingly minor change – an extra π bond – can lead to sign…

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Reaction Friday: Keto-Enol Tautomerism

Reaction Friday: Keto-Enol Tautomerism

April 27, 2012

Today’s Reaction Friday is all about keto-enol tautomersm, the chemistry equivalent of Jekyll and Hyde. Included: Tautomers are constitutional isomers (not resonance forms) The same factors which stabilize alken…

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Another awesome example of acid catalysis: Acids catalyze keto-enol tautomerism

Another awesome example of acid catalysis: Acids catalyze keto-enol tautomerism

May 5, 2010

Between posts on tautomerism and on lewis acid catalysis, I neglected to mention a really important point in carbonyl chemistry that illustrates another facet of acid catalysis: Acids catalyze keto-enol interconversio…

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