Rxn of Iodoethane with Sodium Saccharin

943 words 4 pages
Title: Reaction of Iodoethane with Sodium Saccharin- Ambient Nucleophile
Dates Performed: February 21 + 28, 2013
Date Submitted: March 14, 2013


The product ratio of N-ethylsaccharin to O-ethylsaccharin that occurred due to alkylation with iodoethane at 80 oC was determined to be 81.5% to 18.5%, respectively, based on an analysis of the 1H NMR spectrum that was collected. The melting point range of 87.8-94.7 oC also indicated that the mixture was largely composed of N-ethylsaccharin. The more prevalent product structure is:



N-ethylsaccharin product O-ethylsaccharin product

Experimental Procedure:

Sodium saccharin
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This range is very close to the literature melting point of N-ethylsaccharin. The slight difference in the two could be based on melting point depression that can occur when there is a mixture being analyzed instead of a pure substance, or also could be due to impurities.

1.) If the reaction does not go to completion the residual sodium saccharine or ethyl iodide would not yield both O-ethylsaccharin and N-ethylsaccharin. Since N- ehtylsaccharin is more stable than the O-ethylsaccharin, it would be the major product and only product if the reaction reaches thermal equilibrium. In other words this means that the reaction must go to completion for nucleophilic substitution to occur. Since the oxygen has a higher partial negative charge than the nitrogen atom, the reaction with oxygen as the nucleophile should occur faster. This concludes that if we have residual sodium saccharide and ethyl iodide it would most likely yield O-ethylsaccharin due to the the oxygen being more electronegative than the nitrogen and reacting quicker.

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