Synthesis Lab Report

Soran, Quinn
Dr. Jeffrey Engle
Chemistry 263
5/1/16
Synthesis Project Post-laboratory Report
1. For this experiment, three separate pathways were designed to utilize the exact same reagents in different orders to create a synthesis from acetophenone to methyl m-nitrobenzoate. This experiment was constructed in this format to evaluate the efficiency and overall percent yield of each pathway to determine which is most effective in synthesizing methyl m-nitrobenzoate. The pathway implemented in this experiment used acetophenone as its starting material and converted it to benzoic acid. The benzoic acid was then nitrated to m-nitrobenzoic acid, and the m-nitrobenzoic acid transformed into methyl m-nitrobenzoate.
Benzoic Acid
The first reaction

By comparing the overall percent yields based upon pathway, the statistically superior pathway proved to be the Red pathway, which also happens to be the synthesis pathway I implemented. I determined that this was the best pathway based on the mean, median, and maximum overall percent yields of each pathway and are shown on Table 2. I hypothesize that this pathway was most successful because of the order of the reagents used, specifically that the nitration was the second step. I hypothesize that the addition of the nitro group to the benzoic acid was more successful than other reaction pathways because the attached carboxylic acid group is a moderate deactivator and meta director, more so than the attached ketone in the Blue pathway or the attached ester in the Green

I would suggest to students performing the nitration to make sure their benzoic acid product is very fine and broken up before reacting it, as it has a tendency to clump together when it dries and thus proves very difficult to react in solution. I would also suggest keeping a very close eye on the temperature when adding the sulfuric/nitric acid mixture dropwise, as the reaction has a tendency to spike in temperature