Rxn of Iodoethane with Sodium Saccharin
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
Sodium saccharin …show more content…
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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