2.5 g of potassium hydroxide was added to aqueous solution of 15.0 g potassium p

Question

2.5 g of potassium hydroxide was added to aqueous solution of 15.0 g potassium permanganate. After the potassium hydroxide was dissolved completely, 6.0 g of P Nitrotoluene was added. The reaction mixture was refluxed for 1 h. The mixture was cooled. Treated with 5 to 10 drops of allyl alcohol. The solid formed was separated from reaction mixture by vacuum filtration. The brown solid was washed with water. The filtrate obtained was diluted with water and acidified with 25 mL concentrated hydrochloric acid to afford cream-colored solid after filtration and drying. Yield 65%. The^1H-NMR and IR were recorded. 1. Write a balanced equation 2. Calculate the number of moles of reactants and products. 3. What is the purpose of adding allyl alcohol to reaction mixture before acidification 4. Analyze the^1H-NMR and 1 R spectra of the starting material and the product.

Explanation / Answer

Ans: C7H7NO2 + KMnO4 + KOH -----------------> C7H4KNO4 ------------------> C7H5NO4

137.14 g/mol 158.03 g/mol 56.1 g/mol 205.21 g/mol 167.11 g/mol

6.0 g 15.0 g 25.0 g   65 % Yield (given) = 4.7522 g and 0.0284 moles

   0.0437 moles 0.0949 moles 0.445 moles

Ans 3: The addition of allyl alcohol is done in order to destroy the unreacted oxidizing agents.

Ans 4: 1H NMR: >10 ppm broad singlet -COOH, ~7- 8 ppm two doublets for 2 protons each of benzene ring

IR: 3000-3500 cm-1 broad signal due to O-H stretching owing to Hydrogen bonding, two sharp signals at ~ 1350 and 1550 cm-1 due to -N-O streching

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