Monthly Archives: May 2011

Final Project Spring 2011: Part III

The second synthesis project (performed by a fourth of the class) started out with a reaction we had done a few weeks before. The oxidation of cyclohexanol with household bleach was the lead-off reaction. This was followed by the addition of phenylmagnesiumbromide Grignard reagent to the cyclohexanone. We added a rather large excess of Grignard […]

Final Project: Spring 2011- Part II

The first synthesis project began with the Diels Alder reaction we performed in Fall. The reaction of xylenes with maleic anhydride in refluxing xylenes yields cis-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid anhydride (better known as the “Diels Alder adduct”). This was boiled with aqueous base the following week to yield the dicarboxylic acid. The dicarboxylic acid can be easily […]

Final Project: Spring 2011- Part I

For the final sequence of reactions this semester, students were assigned one of four possible three-step syntheses. The unique thing about these synthesis projects was that they were based on previous reactions that we had done either first or second semester. As I have previously propounded, I feel that it is a good thing for […]

This Little Light of Mine

This year we revisited the “Synthesis of Chemiluminescent Esters” experiment that was performed by a handful of students in Spring 2008. This time the experiment was performed by 65 sophomore organic chemistry students. We followed the protocol published in the Journal of Chemical Education in 2004: Synthesis of Chemiluminescent Esters: A Combinatorial Synthesis Experiment for […]

Esters (and other things) From Boiling Acid

We have been applying a combinatorial scheme to the Fischer esterification synthesis of under-characterized esters for the past few years. This year we combined either 4-methylbenzoic acid, 4-methoxybenzoic acid, or 2-methoxybenzoic acid with either 1-propanol or 2-propanol. The excess alcohol takes the role of both solvent and reagent. The water soluble alcohol is removed by […]