CRSEXP050

=Scheme= acetic anhydride in RA ethanol in RA dimethylformamide in RA ethyl acetate in RA acetic acid in RA esterification in RA

=Researchers= Kayla Gogarty Reaction Attempts

=Objective= To explore the rate of reaction and to observe the products that are produced in a mixture of ethanol, acetic anhydride, and DMF under standard conditions and in the absence of a catalyst via HNMR spectroscopy. CDCl3 was used as the external reference in the outer coaxial NMR tube (the coaxial system has been shown to shift peaks).

=Procedure= [|Calculation Sheet]

=Results= [|CRSEXP050-1] pure acetic anhydride [|CRSEXP050-2] pure ethanol [|CRSEXP050-3] pure dimethylformamide (DMF) Analysis of these three pure spectra prove that the components of the mixture are not pure. The following spectra were taken to determine the impurity in the acetic anhydride bottle. [|CRSEXP050-17] excess acetic anhydride with 1 drop of acetone (CDCl3 as reference) CRSEXP050-18 excess acetic anhydride with 1 drop of acetic acid (CDCl3 as reference) [|CRSEXP050-19] acetic anhydride (excess CDCl3 with one drop of acetone as reference) [|CRSEXP050-2(2)] pure ethanol (from new bottle)

Based on the spectra, there is an acetone impurity in the acetic anhydride bottle.

=Discussion=

=Conclusion=

=Log= Planned sample mixtures and performed calculations CRSEXP050-1: pure acetic anhydride CRSEXP050-2: pure ethanol CRSEXP050-3: pure dimethylformamide (DMF) CRSEXP050-4: 1mmol acetic anhydride (0.09mL), 5mmol ethanol (0.29mL) CRSEXP050-5: 1mmol ethanol (0.06mL), 5mmol acetic anhydride (0.47mL) CRSEXP050-6: 1mmol acetic anhydride (0.09mL), 5mmol DMF (0.39mL) CRSEXP050-7: 1mmol DMF (0.08mL), 5mmol acetic anhydride (0.47mL) CRSEXP050-8: 1mmol ethanol (0.06mL), 5mmol DMF (0.39mL) CRSEXP050-9: 1mmol DMF (0.08mL), 5mmol ethanol (0.29mL) CRSEXP050-10: 1mmol acetic anhydride (0.09mL), 5mmol ethanol (0.29mL), 25mmol DMF (1.94mL) CRSEXP050-11: 1mmol acetic anhydride (0.09mL), 5mmol DMF (0.39mL), 25mmol ethanol (1.46mL) CRSEXP050-12: 1mmol ethanol (0.06mL), 5mmol acetic anhydride (0.47mL), 25mmol DMF (1.94mL) CRSEXP050-13 1mmol ethanol (0.06mL), 5mmol DMF (0.39mL), 25mmol acetic anhydride (2.36mL) CRSEXP050-14: 1mmol DMF (0.08mL), 5mmol ethanol (0.29mL), 25mmol acetic anhydride (2.36mL) CRSEXP050-15: 1mmol DMF (0.08mL), 5mmol acetic anhydride (0.47mL), 25mmol ethanol (1.46mL) 9:50-HNMR of pure samples (CRSEXP050-1, CRSEXP050-2, CRSEXP050-3) 16 scans, 1second relaxation delay, 45 degree pulse angle, CDCl3 as solvent Analysis of HNMR shows that these mixture components are not pure Planned sample mixtures to determine impurity in acetic anhydride CRSEXP050-17: excess acetic anhydride with 1 drop of acetone (CDCl3 as reference) CRSEXP050-18: excess acetic anhydride with 1 drop of acetic acid (CDCl3 as reference) CRSEXP050-19: acetic anhydride (excess CDCl3 with one drop of acetone as reference) CRSEXP050-2(2): pure ethanol (from new bottle) HNMR of samples (CRSEXP050-17, CRSEXP050-19, CRSEXP050-2(2)) 9:30: 8 scans, 1second relaxation delay, 45 degree pulse angle, CDCl3 as solvent Analysis of HNMR shows that there is an acetone impurity in the acetic anhydride bottle
 * 14-05-01**
 * 14-05-02**
 * 14-05-05**
 * 14-05-12**