1.0 g of vanillin was dissolved in 20 mL of ethanol. To this solution, 1.17 g of
ID: 517441 • Letter: 1
Question
1.0 g of vanillin was dissolved in 20 mL of ethanol. To this solution, 1.17 g of sodium iodide was added, then cooled to 0 °C with an ice/water bath. 11.0 mL of aqueous sodium hypochlorite solution (5.25% w/w) was added dropwise to the stirred reaction mixture at a rate of 1 drop per second. Once the addition was complete, the mixture was warmed to room temperature and stirred for 10 minutes.Then, 10 mL of sodium thiosulfate solution (10% w/v) was added, then 6 mL of 3M hydrochloric acid was added. The aryl iodide should precipitate at this point.The ethanol was removed using a rotary evaporator. The flask was cooled for 10 minutes, then the precipitate was collected through vacuum filtration. Crude product was weighed to be 1.92 grams. The product was recrystallized from ethanol and the recrystallized product mass was recorded to be 0.83 grams.
A common method for the iodination of aromatics is the use of I2 and nitric acid. List specific advantages of the method you have used in this experiment (NaI/NaOCl). Hint: do research and consider the hazards of each method.
Explanation / Answer
The advantage are:
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