Grignard Reaction - Synthesis of Substituted Benzoic Acids

A convenient preparation of substituted benzoic acids from Grignard additions to solid carbon dioxide. Students create a library of carboxylic acids by using differentially substituted, commercially available aryl bromides, which can be used as the starting materials for a multistep synthesis. This is a modification and improvement of a very popular undergraduate organic chemistry experiment.

Kinetic Analysis of Ester Hydrolysis

A two-week multi-step experiment that introduces students to mechanistic organic chemistry and substituent effects. A simple preparation of differentially substituted para-nitrophenyl benzoates is followed by ester hydrolysis with monitoring by UV-Vis spectroscopy to provide rate data for the reaction.

Borohydride Reduction of Fluorenone

A simple experiment to demonstrate nucleophilic addition to a carbonyl. Sodium borohydride-mediated reduction of fluorenone is a fast and high-yielding reaction that is suitable for beginning students. Students isolate their fluorenol product by recrystallization and characterize it by NMR and IR.