Question 1
What is the predicted major product when pyridine is treated with a mixture of nitric acid and sulfuric acid?
◦ 4-aminopyridine
◦ 4-nitropyridine
◦ 2-nitropyridine
◦ 2,3-dinitropyridine
◦ 3-nitropyridine
Question 2
A compound with molecular formula C
8H
10BrN exhibits a singlet at δ 1.2 (2H), a triplet at δ 2.8 (2H), a triplet at δ 3.0 (2H), a doublet at δ 7.1 (2H) and a doublet at δ 7.4 (2H) in its
1H NMR spectrum. Its IR spectrum shows two medium absorption bands near 3400 cm
-1. What is the structure for this compound?
![](data:image/png;base64, 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◦ I
◦ II
◦ III
◦ IV
◦ V