Catalyst Selectivity in the Addition of Hydroxybenzoic Acids to Glycidyl Phenyl Ether
Category
High School
Department
Undeclared
Student Status
High School
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
Epoxides are an important class of reagents in organic chemistry which react with a variety of nucleophiles. Strong nucleophiles add to epoxides at the least substituted carbon via a SN2 mechanism. However, under acidic conditions nucleophilic addition is at the most substituted carbon via a SN1 mechanism. Included within this class of reactions is the addition of carboxylic acids or phenols 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 showed a faster reaction rate of benzoic acid addition to an epoxide with tetrabutylammonium fluoride. Due to this result, we were interested in the effect of catalyst on the selectivity of the reaction. To glycidyl phenyl ether was added 4-hydroxybenzoic acid, 3-hydroxybenzoic acid or salicylic acid using a tetrabutylammonium halide (F, Cl, Br, or I) catalyst. After the reaction, the products were analyzed by IR spectroscopy and the product ratio was determined using proton NMR spectroscopy. The resulting IR spectra and ratio of products from these studies will be reported.
Catalyst Selectivity in the Addition of Hydroxybenzoic Acids to Glycidyl Phenyl Ether
Student Center Ballroom
Epoxides are an important class of reagents in organic chemistry which react with a variety of nucleophiles. Strong nucleophiles add to epoxides at the least substituted carbon via a SN2 mechanism. However, under acidic conditions nucleophilic addition is at the most substituted carbon via a SN1 mechanism. Included within this class of reactions is the addition of carboxylic acids or phenols 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 showed a faster reaction rate of benzoic acid addition to an epoxide with tetrabutylammonium fluoride. Due to this result, we were interested in the effect of catalyst on the selectivity of the reaction. To glycidyl phenyl ether was added 4-hydroxybenzoic acid, 3-hydroxybenzoic acid or salicylic acid using a tetrabutylammonium halide (F, Cl, Br, or I) catalyst. After the reaction, the products were analyzed by IR spectroscopy and the product ratio was determined using proton NMR spectroscopy. The resulting IR spectra and ratio of products from these studies will be reported.
