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Essay about Rxn of Iodoethane with Sodium Saccharin

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

Abstract:

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:

C2H5I
C2H5I

And/Or
And/Or

N-ethylsaccharin product O-ethylsaccharin product

Experimental Procedure:

Sodium saccharin …show more content…

N- saccharin is more stable than O-saccharin, so it should be the major product of the reaction, if not the only product, if the reaction reaches thermal equilibrium. A reaction involving the oxygen as the nucleophile should occur faster than one involving nitrogen because the oxygen is more electronegative. This electronegativity would attract the attack of the nucleophile more so than the Nitrogen atom would. Based on the 1H NMR spectrum that was collected, a few things can be determined. Based on deshielding and electronegativity, the peak that occurs around 4.7ppm is associated with the O-ethylsaccharin product and the peak at 3.8 ppm is associated with the N-ethylsaccharin product. Based on the height ration, the N-ethylsaccharin product is the more prevalent result. The solvent that was chosen for the experiment is a polar aprotic solvent that can be used to stabilize charge. This stabilization can also be used to stabilize an ionic transition state. This stabilization of the transition state along with the nature of the products based on the chemical properties would encourage the reaction to proceed toward the N-ethylsaccharin product. This product is more stable

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