Wolffenstein–Böters reaction

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The Wolffenstein–Böters reaction is an interesting organic reaction where benzene is converted to picric acid by using a mixture of aqueous nitric acid and mercury(II) nitrate.

Mechanism

The reaction has not been investigated thoroughly, but research done show the following: benzene is converted to the corresponding nitroso compound by the mercury(II) nitrate and through the diazonium salt to the phenol. The presence of nitrite is essential for the reaction; picric acid formation is prevented when urea, a trap for nitrous acid, is added to the mixture. From then on the reaction proceeds as a regular aromatic nitration.[1]

Procedure

Projects

  • Make picric acid

Safety

Mercury(II) nitrate is extremely toxic and proper protection must be worn when handling the compound.

References

  1. https://en.wikipedia.org/wiki/Wolffenstein%E2%80%93B%C3%B6ters_reaction

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