Friday 26 February 2016

organic chemistry - Hydrolysis of Sucrose over Sn1Ac or Sn2Ac



In "March's Advanced Organic Chemistry" I have read about the general mechanism of the acetal hydrolysis. It names the acid-catalyzed SN1 or SN2 as a possible mechanism for a Acetal-hydrolysis.


Now I am interested to know if SN1 or SN2 is mainly going on at the Hydrolysis of Sucrose to Glucose and Fructose. So I compared the different parameters which influence SN1/SN2.




  • Polarity of the solvent: Water -> really polar -> SN1 preferred.




  • Stabilization of a possible Carbokation-Intermediat: Primary (Anomeric C!), so not really stabilized by Hyperconjunction -> SN2 preferred. (Is there Hyperconjunction also in the ether-O?)





  • Mesomeric stabilization There is also a mesomeric stabilization between the resulting carbocation and a Oxonium-Ion in the SN1-Mechanism.




  • Steric Hindrance: In my opinion, through the planar region around the anomeric C (planar ether), there is no steric hindrance -> SN2 possible.




  • Temperature: high temperature -> SN1 preferred.




So to conclude: Many different aspects. Because of the main points "steric hindrance" and the destabilized primary carbocation intermediate I would conclude that the hydrolysis of Sucrose goes mainly (maybe a little bit over SN1) over SN2.



Have I forgotten something important? Are my assumptions "No steric hindrance" and primary carbocation-intermediate correct?


I have attached my possible SN1-mechanism.





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