IOM 2021, Блиц — Задача 76

The Blitz-contest of IOM-2021

Условие

Arrange in the correct order the steps for the selective synthesis of ortho-nitrophenylacetic acid from toluene. Only one organic product should be obtained at each stage. Some stages may be used several times, and some may not be used at all. Enter the sequence of numbers without spaces, for example: 12344321.

Reaction scheme: toluene (a benzene ring with CH3) → (arrow) a benzene ring with CH2COOH and, on the neighbouring (ortho) carbon, NO2.

  1. NaCN\mathrm{NaCN}

  2. H2SO4(conc.), t∘\mathrm{H_2SO_4(conc.),\ t^{\circ}}

  3. HNO3(conc.), H2SO4(conc.), t∘\mathrm{HNO_3(conc.),\ H_2SO_4(conc.),\ t^{\circ}}

  4. Br2,hν\mathrm{Br_2, h\nu}

  5. Br2,FeBr3,t∘\mathrm{Br_2, FeBr_3, t^{\circ}}

  6. H2SO4,H2O, t∘\mathrm{H_2SO_4, H_2O,\ t^{\circ}}

Отговори

Решение

Оригинал в Архива: iom-2021-blitz-tasks-eng.pdf · официални решения: iom-2021-blitz-answers-eng.pdf