Acid-Catalyzed Enolization of β-Tetralone

摘要

This experiment allows students to use 1H NMR to directly compare the relative initial rates of substitution of the benzylic and non-benzylic α hydrogens of β-tetralone and correlate their findings with the predictions made by resonance theory. The experiment demonstrates that the benzylic hydrogens undergo α substitution much faster than the non-benzylic hydrogens. The described experiment can be used in the introductory two-semester organic chemistry course sequence to make the concepts of enolization and resonance concrete.