13C NMR Analysis of an Aqueous Electrophilic Aromatic Substitution (Synthesis of β-Resorcylic Acid) (Journal Article)
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 .
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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.
0021-9584
RIEBPL Library
Second-Year Undergraduate
Upper-Division Undergraduate
Organic Chemistry Laboratory
Instruction NMR Spectroscopy
Green Chemistry Hands-On Learning/Manipulatives
540.7
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 .
***______________***
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.
0021-9584
RIEBPL Library
Second-Year Undergraduate
Upper-Division Undergraduate
Organic Chemistry Laboratory
Instruction NMR Spectroscopy
Green Chemistry Hands-On Learning/Manipulatives
540.7