Carbocation Rearrangement in an Electrophilic Aromatic Substitution Discovery Laboratory

  title={Carbocation Rearrangement in an Electrophilic Aromatic Substitution Discovery Laboratory},
  author={V. Polito and C. S. Hamann and Ian J. Rhile},
  journal={Journal of Chemical Education},
In this discovery laboratory, students performed electrophilic aromatic substitution reactions between 1,4-dimethoxybenzene and either 2-methyl-2-butanol or 3-methyl-2-butanol with sulfuric acid as a catalyst. The carbocation from 3-methyl-2-butanol undergoes a hydride shift, and hence, both reactions afford 1,4-bis(1,1-dimethylpropyl)-2,5-dimethoxybenzene in high yields. NMR spectroscopy, infrared spectroscopy, mass spectrometry, and the melting point all indicate identical products from both… Expand
Synthesis of Methyl Cyclopentanecarboxylate: A Laboratory Experience in Carbon Rearrangement
We present a novel guided inquiry second semester organic chemistry laboratory rearrangement experiment. Students performed the Favorskii Rearrangement to obtain methyl cyclopentanecarboxylate inExpand
  • Kiichi Amimoto
  • Chemistry, Medicine
  • Acta crystallographica. Section E, Structure reports online
  • 2011
The title compound, C18H30O2, was prepared by Friedel–Crafts alkylation of 1,4-dimethoxybenzene with 2-methyl-2-butanol with the application of a crystallographic centre of inversion. Expand
Synthesis of Bisphenol Z: An Organic Chemistry Experiment
A student achievable synthesis of bisphenol Z, 4,4′-(cyclohexane-1,1-diyl)diphenol, from the acid-catalyzed reaction of phenol with cyclohexanone is presented. The experiment exemplifies all theExpand
Electrostatic Potential Maps and Natural Bond Orbital Analysis: Visualization and Conceptualization of Reactivity in Sanger's Reagent.
Frederick Sanger’s early work on protein sequencing through the use of colorimetric labeling combined with liquid chromatography involves an important nucleophilic aromatic substitution (SNAr)Expand