N-methyl-2-pyrrolidone is an aprotic solvent used in many industrial processes. draw the structure of the product formed when it is

Question

N-methyl-2-pyrrolidone is an aprotic solvent used in many industrial processes. draw the structure of the product formed when it is heated with aqueous acid.

Rose Schowalter · Accepted Answer

We will obtain 4-(methylamino)butanoic acidExplanation:In the heating process of the N-methyl-2-pyrrolidone in acid medium, the oxo group will attack the hydronium ion to produce a cation in the oxygen. Then we will have a delocalization of the double bond upon the oxygen generating a carbocation. A continuation the water will attack the carbon cation producing a new C-O bond and a positive charge in the oxygen. The next step would be the attack of the lone pair from the nitrogen to the H generating a positive charge in the nitrogen. Then the N-C bond would break and the lone pair of the oxygen would attack the carbon regenerating the oxo group (C=O). Finally, the hydronium ion would leave the molecule producing the 4-(methylamino)butanoic acid. To further explanations check the attached image.

Mr. Bertha Ziemann IV

N-methyl-2-pyrrolidone is an aprotic solvent used in many industrial processes. draw the structure of the product formed when it is

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