Rxn of Iodoethane with Sodium Saccharin

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 (0.446 g) was dissolved in N-N-dimethylformamide (DMF) at 80oC. Iodoethane (0.16 mL) was added and heated at constant temperature (80oC) for ten minutes. The product was separated by adding water to the room temperature solution, further cooled in ice and the solid collected and dried via vacuum filtration. The following week, the dried product (0.442g) was analyzed by melting point (87.8-94.7oC), and a 1H NMR spectrum.

Data and Calculations:

Table 1: Reactant and Product Masses and Properties | Mol mass (g/mol) | Bp (oC) | Mp (oC) | Density (g/mL) | Amount to use | Sodium saccharin | 223 | | | | 0.002 mol, 0.446 g | Iodoethane | 156.0 | 72 | | 1.95 | 0.002 mol, 0.78 g | N-N-Dimethylforammide (DMF) | 73.1 | 153 | | 0.945 | 1.0 mL | N-ethylsaccharin | 211.2 | | 95 | | | O-ethylsaccharin | 211.2 | | 211 | | |

Table 2: 1H NMR Ha | 3.8 ppm, quartet | Hb | 4.7 ppm, quartet |

Theretical Yield=0.002 mol sodium saccharin1 mol product1 mol sodium saccharin=0.002 mol x 223g1 mol=0.446 g

% yield= actual masstheoretical mass=0.442g0.446g=0.9910x 100%=99.1% yield

Vial with product: 7.619 g
Empty vial -7.177 g 0.442 g product yielded

NMR Data: