Chapter 19.SE, Problem 47MP

Interpretation Introduction

Interpretation:

A mechanism for the formation of 3,5-dimethyl-oxazole from hydroxylamine and 2,4-pentanedione is to be proposed.

Concept introduction:

One of the keto group in the diketone will react with hydroxyl amine to yield an oxime. The nucleophilic attack of the amino group of the oxime, internally, on the other carbonyl group followed by abstraction of a proton by the carbonyl oxygen and subsequent deprotonation of the protonated oxazole obtained will yield 3,5-dimethyloxazole.

To propose:

A mechanism for the formation of 3,5-dimethyloxazole from hydroxylamine and 2,4-pentanedione.