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Please answer the following as detailed as possible. (PLEASE do not answer if yo

ID: 1040945 • Letter: P

Question

Please answer the following as detailed as possible. (PLEASE do not answer if you are uncertain of the solution, thank you)

1. The synthesis of N-phenylphthalimide was performed by an student according to the following reaction: (6 points) Phthalic acid and aniline were heated to reflux for one hour. Upon cooling, the mixture was dissolved in ether and placed in a separatory funnel. The solution was then washed with 5% aqueous Na2CO3 followed by 5% aqueous HCl and allowed to stand over solid anhydrous Na2S04 for 15 minutes. The ether was then evaporated and a solid product obtained. The crude product was dissolved in an appropriate hot solvent and after slowly cooling the solution, crystals were obtained, which after filtering and drying gave a melting point of 205 to 207 °C. The literature value for the melting point of the expected product is 208 °C. C-OH +2H,O C OH 0 Phthalic acid Analine N- Phenylphthalimide A. In the experiment, which of the following would have been removed by washing the solution with sodium carbonate? B. What was the purpose of allowing the washed product mixture to stand over solid anhydrous sodium sulfate? C. What conclusion can be drawn from the melting point data given in the passage?

Explanation / Answer

A. Washing with sodium carbonate solution, any acid compound taken iin round bottom flflask is remained as such is removed as sodium phthalate.

b. On standing the washed precipitate on sodium sulfate the ccompound is dried by dehydration because anhydrous sodium sulfate acts as a dehydrating agent.

c. The melting point of 205 to 208 degree celcius is due to some impurities present in final product