Effect of Ammonium Salts in the Addition of Benzoic Acid to Glycidyl Phenyl Ether
Category
Sciences and Technology
Department
Chemistry
Student Status
Undergraduate
Research Advisor
Dr. Jody Neef
Document Type
Event
Location
Student Center Ballroom
Start Date
10-4-2025 2:00 PM
End Date
10-4-2025 4:00 PM
Description
Nucleophilic additions to epoxides are an important class of reactions in organic chemistry which have found use in material science, as intermediates, and in the synthesis of biologically important compounds. Many nucleophiles add to epoxides via a SN2 mechanism at the least substituted carbon. However, under acidic conditions addition is at the most substituted carbon via a SN1 mechanism. Included within this class of reactions is the addition of carboxylic acids to epoxides using tetrabutylammonium bromide as the catalyst. These reactions are straight forward and give high yields of the product. However, previous work in our lab using phthalimide as the nucleophile showed a faster reaction rate with tetrabutylammonium fluoride. Due to this result, we were interested in studying the effect of ammonium salts on the addition of benzoic acid to glycidyl phenyl ether. To better understand this reaction and the role of the catalyst, the halide of the ammonium salt was varied (F-, Cl -. Br, and I ), in addition to the alkyl groups length (Bu, Pr, Et, Me). Reaction times were determined by IR spectroscopy and the product ratio was determined using proton NMR spectroscopy. The results, reaction times and product(s), of these studies will be reported.
Effect of Ammonium Salts in the Addition of Benzoic Acid to Glycidyl Phenyl Ether
Student Center Ballroom
Nucleophilic additions to epoxides are an important class of reactions in organic chemistry which have found use in material science, as intermediates, and in the synthesis of biologically important compounds. Many nucleophiles add to epoxides via a SN2 mechanism at the least substituted carbon. However, under acidic conditions addition is at the most substituted carbon via a SN1 mechanism. Included within this class of reactions is the addition of carboxylic acids to epoxides using tetrabutylammonium bromide as the catalyst. These reactions are straight forward and give high yields of the product. However, previous work in our lab using phthalimide as the nucleophile showed a faster reaction rate with tetrabutylammonium fluoride. Due to this result, we were interested in studying the effect of ammonium salts on the addition of benzoic acid to glycidyl phenyl ether. To better understand this reaction and the role of the catalyst, the halide of the ammonium salt was varied (F-, Cl -. Br, and I ), in addition to the alkyl groups length (Bu, Pr, Et, Me). Reaction times were determined by IR spectroscopy and the product ratio was determined using proton NMR spectroscopy. The results, reaction times and product(s), of these studies will be reported.
