Question

Sulfapyridine (once known as M&B 693) was one of the first generation sulfanilamide antibiotics and was used to successfully treat Winston Churchill's bacterial pneumonia during the height of World War 2 in 1943. Sulfapyridine can be synthesized in two steps from 2-bromopyridine. Br NaNH2 NH2 X (a sulfonyl chloride) pyridine 2-bromopyridine 2-aminopyridine H2N sulfapyridine (M&B 693) a. Provide a detailed, arrow-pushing mechanism (show all arrows) by which 2-bromopyridine is converted to 2-aminopyridine upon treatment with sodium amide (NaNH2). Show all relevant resonance structures to receive full credit. [7 points] b. 2-aminopyridine reacts with sulfonyl chloride X in the presence of pyridine to give sulfapyridine. Give the structure of X and provide a detailed, arrow-pushing mechanism for its reaction with 2-aminopyridine. [11 points)