Question

1. Compare the melting point of phenacetin you obtained with the literature value. If your melting point is significantly different than literature value (more than 5 °C), comment what the reason could be.?

2. Suppose a student mistakenly used sodium bicarbonate (NaHCO3) as a base, instead of potassium carbonate in reaction of phenol with iodoethane. Did (s)he get the expected ether? Explain briefly why.

Answer 1

1. Answer

The melting point of phenacetin obtained is more than 5⁰C when compare to the literature melting point. The reason for the increase in melting point is due to the impurity of p-acetaminophenol impurity present is very small amount which is having higher melting point than phenacetin. Impurity present in the compound will change the melting point.

2. Answer

Sodium bicarbonate is not a strong enough base to remove a hydrogen ion from phenol. So when we are treating phenol with ethyl iodide in presence of NaHCO₃ reactions will not takes place doesn’t get ester.