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nitricmethylnitrotoluenetoluene

video tutorial Nitrotoluene from the mixed acid nitration of toluene

  • Overview: Nitration of toluene with mixed nitric/sulfuric acid to yield mainly nitrotoluene, favoring the para isomer by temperature control.
  • Key principles: activated ring by methyl group; low temperature and slow acid addition reduce side products; electrophilic aromatic substitution.
  • General procedure (high-level): prepare nitrating mixture, add toluene in an ice bath, carefully add acid while monitoring temperature to keep below about 15°C, then allow reaction to finish and warm to room temperature with stirring; separate organic vs acid phases.
  • Workup: wash organic product with water and sodium bicarbonate to remove acids; dry the product with calcium chloride; obtain a crude nitro-toluene mixture.
  • Purification: freeze-thaw/evaporation/crystallization to isolate para-nitrotoluene, using repeated crystallization to improve purity; note that full separation of isomers by simple distillation is impractical due to close boiling points.
  • Outcome: para-nitrotoluene crystals, with typical notes on odor and appearance; procedure adapted from OC Practicum.

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