2. The oxime 6 was treated with sulfuric acid in an attempt to form the eight- membered lactam 7. The spectroscopic data

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2 The Oxime 6 Was Treated With Sulfuric Acid In An Attempt To Form The Eight Membered Lactam 7 The Spectroscopic Data 1 (44.08 KiB) Viewed 13 times

2. The oxime 6 was treated with sulfuric acid in an attempt to form the eight- membered lactam 7. The spectroscopic data (listed below) for the product isolated indicates the desired compound 7 was not formed. Explain why the data is inconsistent with the expected product, and suggest an alternative structure for the actual compound 8 formed, assigning the data as fully as possible. Give a mechanism for its formation and suggest why the expected product 7 was not formed. HON H2SO4 H2SO4 8 7 Compound 8: Зн 7.44 (1H, dd, J7, 1), 7.36 (1H, dd, J8, 1), 7.25 (1H, dd, J8, 7), 2.57-2.54 (2H, m) 1.55-1.51 (2H, m), 1.48-1.46 (2H, m), 1.20 (6H, s). Vmax 2200 cm m/z 185 (M), 170, 159. [25 marks]