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Fundamentals of Organic ChemistryChemistryAlcohols Phenols and Ethers

2,4,6-Trinitrophenol (picric acid) can be prepared in good yield by:

Options

  1. Aboth of these methods
  2. Bneither of these methods
  3. Cthe nitration of 2,4-dinitrophenol
  4. Dthe nitration of 2,4-dinitrochlorobenzene

Correct answer

C. the nitration of 2,4-dinitrophenol

Step-by-step solution

Direct nitration of phenol with concentrated nitric acid gives a poor yield of 2,4,6-trinitrophenol (picric acid) due to extensive oxidation of the highly activated aromatic ring. To achieve a good yield, the ring must be deactivated prior to the final nitration step. This is commonly done by first synthesizing 2,4-dinitrophenol (often from the hydrolysis of 2,4-dinitrochlorobenzene). The nitration of 2,4-dinitrophenol proceeds smoothly to give picric acid in good yield because the presence of two strongly electron

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