Carbocation Rearrangement in an Electrophilic Aromatic Substitution Discovery Laboratory

@article{Polito2010CarbocationRI,
  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},
  year={2010},
  volume={87},
  pages={969-970}
}
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
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1,4-Bis(1,1-dimethylpropyl)-2,5-dimethoxybenzene
  • Kiichi Amimoto
  • Chemistry, Medicine
  • Acta crystallographica. Section E, Structure reports online
  • 2011
TLDR
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
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