Kayla+Gogarty+Winter+2014


 * Winter 2014**

This term, I continued performing CRS experiments. Throughout the term, I examined several reactions with acetic anhydride. The first reaction was acetic anhydride with an aromatic aldehyde, Phenanthrene-9-carboxaldehyde. This experiment can be found here. Unfortunately, Phenanthrene-9-carboxaldehyde is a solid, making it difficult to get a pure HNMR spectrum. Therefore, only HNMR spectra of acetic anhydride and two mixtures were taken. Based on the HNMR spectra, it does not appear that a reaction occurred.

The second reaction that I performed was acetic anhydride with heptylamine. HNMR spectra of five mixtures were taken. These five mixtures included pure acetic anhydride, pure heptylamine, half by volume mixture of the two, one drop acetic anhydride in excess heptylamine, and one drop of heptylamine in acetic anhydride. When these two chemicals were combined, an immediate reaction occurred and heat and white gas were produced. This reaction produced N-heptylacetamide very rapidly and therefore, a catalyst is not required for this reaction. The reaction between acetic anhydride and heptylamine occurs very rapidly, even without a catalyst. The HNMR spectra at 20 minutes and 19 hours look identical, which proves that the reaction is complete within 20 minutes. When mixing the reagents, heat and white gas were immediately produced. Based on literature searches, this reaction is not performed very often. performed the reaction to determine whether the product, N-heptyl acetamide, would be a useful insecticide and/or acaricide. The reactions they performed were under suitable conditions. As proven by the experiment, this reaction does not require a catalyst because it reacts very rapidly when the reagents are simply mixed.

Another reaction that I performed was acetic anhydride with cyclohexanol. HNMR spectra of five mixtures were taken. These five mixtures included pure acetic anhydride, pure cyclohexanol, half by volume mixture of the two, one drop acetic anhydride in excess cyclohexanol, and one drop of cyclohexanol in acetic anhydride. Based on the HNMR spectra, the peaks for the product are bigger after 24 hours than after 15 minutes. Therefore, the reaction was not complete after 15 minutes and the reaction occurs slowly without a catalyst. Based on literature searches, this reaction is performed often with various organic and inorganic catalysts. performed the reaction without a catalyst and under solvent-free condition. However, the researchers used a microwave to induce a rapid reaction. Under these conditions, the reaction occurred 6 minutes after mixing the reagents and there was an 84% yield. Therefore, the presence of microwaves causes the reaction to occur more rapidly. Without microwaves, the reaction performed slowly without a catalyst.

Next term, I will continue to work on the Chemical Rediscovery Survey. I would like to continue analyzing reactions with acetic anhydride to see if there are any other reactions that occur as rapidly as the reaction with heptylamine without a catalyst.

A complete list of the experiments I have performed throughout the year can be found [|here].