1. Chapter 28 Nitration of Methyl Benzoate

2. Purpose In this experiment a cold solution of an aromatic ester that has been in sulfuric acid is reacted with nitric acid. This highly exothermic reaction is controlled by cooling; then the mixture is poured on ice.In this experiment a cold solution of an aromatic ester that has been in sulfuric acid is reacted with nitric acid. This highly exothermic reaction is controlled by cooling; then the mixture is poured on ice. The solid product is isolated by filtration and washing with water.The solid product is isolated by filtration and washing with water.

3. Reaction Mechanism The nitration is a typical electrophilic substitution reaction. The electrophile is nitronium ion (NO 2 + ) generated by the reaction of concentrated sulfuric and nitric acids.The nitration is a typical electrophilic substitution reaction. The electrophile is nitronium ion (NO 2 + ) generated by the reaction of concentrated sulfuric and nitric acids.

4. Comments Follow pp. 432-433(microscale).Follow pp. 432-433 (microscale). Follow the lab handout for all experimental procedures. Wearing rubber gloves is absolutely necessary during this lab! You will work with toxic and corrosive acids.Follow the lab handout for all experimental procedures. Wearing rubber gloves is absolutely necessary during this lab! You will work with toxic and corrosive acids. Perform IR analysis of the product.Perform IR analysis of the product. Calculate yield. Moderate yields should be achieved.Calculate yield. Moderate yields should be achieved. (Moles Product / Moles Starting Material) x 100 = % Yield

5. Safety Concentrated H 2 SO 4 and HNO 3 are corrosive and toxic, wear gloves and handle with care.Concentrated H 2 SO 4 and HNO 3 are corrosive and toxic, wear gloves and handle with care. Make sure to slowly add concentrated sulfuric acid into the concentrated nitric acid (not vice versa!!!). Use extreme caution.Make sure to slowly add concentrated sulfuric acid into the concentrated nitric acid (not vice versa!!!). Use extreme caution.