Final Project Spring 2011: Part VI

The lab report for the final project was submitted as a JOC style article. The students had been writing parts of their lab reports in scientific article format during the semester: Abstract, Introduction, Results and Discussion, Conclusion, Experimental Section, and of course References. This was the first time I had given this type of assignment […]

Final Project Spring 2011: Part V

The fourth synthesis project started with the dehydration of cyclohexanol. We had performed the dehydration of 2-methylcyclohexanol during the Fall semester. The resulting cyclohexene was oxidized by hydrogen peroxide in the presence of a phase-transfer catalyst. This reaction was featured in a 2000 JCE article. There was some unreacted cyclohexanol with the cyclohexene but that […]

Final Project Spring 2011: Part IV

The third project started with the synthesis of an azo dye that we had performed earlier in the semester. The combination of 4-aminosulfonic acid and 2-naphthol yields 4-(2-hydroxy-1-naphthylazo)benzenesulfonic acid which is also known as acid orange 7. The phenolic hydroxyl group was acetylated with acetic anhydride in a reaction which is similar to the one […]

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 […]

We are Dyeing to Know More About EAS

I have doing a variation of the “methyl orange” azo dye synthesis in organic lab for the past ten years. Lately, we have performed a combinatorial scheme involving the three aminobenzenesulfonic acids and 1- or 2-naphthol. This was inspired by a 2004 article in J. Chem. Ed. by Gung and Taylor. This year, for the […]

Ether One or the Other

This year we performed the synthesis of triphenylmethanol with a commercial phenylmagnesium bromide reagent. The reaction, in principle, works quite well and the reaction turns a pretty pink color on the way to completion. This year, the class was divided into three groups and each group used a different ether solvent for the reaction – […]