Category Archives: Spring 2009 Chemistry Lab

Student Comments Spring 2009

This week I read through the student comments for the Spring 2009 semester. I have just finished posting them on the OChemOnline wiki. It was fun to read how the personality of the students came out in their comments. Some are self-depreciating – “don’t do the same stupid thing I did.” Others are analytical – […]

Gallate Diesters

The products from the acid catalyzed Fischer esterification of gallic acid with isopropanol (see “Fantastic Fischer” April 25, 2009) was chromatographed to purify isopropyl gallate. In addition to isopropyl gallate, another chromatographic peak was observed. This peak was collected and the NMR performed. Interestingly, this spectrum displayed three aromatic hydrogen signals at 7.207 (d), 7.153 […]

New Results for the Dehydration of Methylcyclohexanols

This Spring, a research project was performed by one of my Sophomore Organic Chemistry students. The research project was designed to continue investigations into the dehydration of methylcyclohexanols that we explored Fall 2008. I have written several entries for this project, and will likely write several more. In short, the simple dehydration of an alcohol […]

Chemical “Luminol”escence

The synthesis of Luminol is a great final experiment to cap off a year of organic chemistry laboratory work. It’s a relatively “old” experiment, I did it as in undergraduate. (Adapted from Experiment 48: Luminol, in Pavia, Lampman and Kriz, “Introduction to Organic Laboratory Techniques: A Contemporary Approach” (1976) Saunders.) The procedure involves a two-step […]

Fantastic Fischer

We are again using a very old reaction, mineral acid catalyzed Fischer Esterification, to synthesize new compounds. Last year we synthesized propyl 2-methylbenzoate, propyl 4-methylbenzoate, and propyl 4-methoxycinnamate which have not been characterized by modern spectroscopic methods. This year I replaced 4-methoxycinnamic acid with gallic acid and added 2-propanol to the list of alcohols. Isopropanol […]

The Ancient Art (& Science) of Fermentation

Fermentation of alcoholic beverages is one of the oldest human technologies. Fermentation is also an interesting and educational laboratory exercise that can be done with all levels of students. I even do a fermentation lab with my Language Arts and Sciences summer course! The attraction of fermented beverages for college students does not need a […]

The Gallivanting Grignard

After last year’s “discovery” of the commercially available phenylmagnesiumbromide, I decided to branch out to more interesting reactant than benzophenone. (One redeeming feature of the Grignard synthesis of triphenylmethanol was the pink coloration of the reaction mixture.) This year we used the three positional isomers of methycyclohexanone as the ketone reagent. The resulting methylphenylcyclohexanols are […]

Getting It Right the Second Time

This past week my Organic Chemistry students were instructed to repeat last week’s experiment (oxidization of a secondary alcohol to a ketone with household bleach). They were asked to change one variable that they thought would give a better outcome. I explained that in a real research environment chemical reactions are repeated several times to […]

The Design of Laboratory Experiments in the 2000’s

Last week we did a variation of the oxidation of alcohols with household bleach (sodium hypochlorite) experiment. In the past we have used isoborneol as our alcohol which gave the distinctive smelling solid camphor. This year we had a series of 2, 3, or 4-methyl-1-cyclohexanols as our starting materials so the products were liquid 2, […]

Colorimetric Chemistry

Color chemistry has a long and illustrious history. I, myself can trace my academic ancestry back to William H. Perkin, the inventor of mauvine. Organic Chemistry student can share in this legacy by performing the Azo Dye experiment. The experiment I current use is an extension of the popular methyl orange experiment that I remember […]