01725nam a22002657a 4500 20231116095809.0 231020b ||||| |||| 00| 0 eng d 0021-9584 RIEBPL Library 540.7 James A. McKee et al... 13C NMR Analysis of an Aqueous Electrophilic Aromatic Substitution (Synthesis of β-Resorcylic Acid) (Journal Article) USA :American Chemical Society August 2023 2981-2985 P. American Chemical Society, Volume 100, Issue 8 ***______{For Hard Copy, Please visit Library.}________*** Abstract Electrophilic aromatic substitution reactions are common in the organic chemistry laboratory. These reactions, while ubiquitous, use corrosive reagents and halogenated or hydrophobic solvents that produce expensive and hazardous waste streams. The carboxylation of phenols (Kolbe–Schmitt reaction), although aqueous, typically involves conditions (high pressure/temperature) that are not well-suited for a large teaching laboratory. The following experiment modifies the Kolbe–Schmitt process for ambient pressures and aqueous reflux temperatures. This procedure is safe, simple, and inexpensive and uses 13C NMR as an analytical tool to confirm product synthesis and investigate changes in molecular symmetry. Second-Year Undergraduate Upper-Division Undergraduate Organic Chemistry Laboratory Instruction NMR Spectroscopy Green Chemistry Hands-On Learning/Manipulatives https://pubs.acs.org/doi/epdf/10.1021/acs.jchemed.2c00165 PER 0 0 0 0 RIEBPL RIEBPL 2023-11-16 0 540.7 2023-11-16 00:00:00 2023-11-16 PER 44875 44874