When reacting the molecule below with xs Methanol in 3eq of H2SO4 with benzene and distillation then washed with NaHCO3. It forms a product of C5H9NO (I'm sorry that's a lot of reagents). Some spectral data: IR- 3219, 2944, 2866, 1666. C13 - 173, 42, 31.5, 22.3, 20.9. H NMR 7.40 (1H, s), 3.31 (2H, m), 2.34 (2H, m), 1.75 (4H, m). I thought it may form one of the rings below, but I am not sure if you can have ring metathesis in this reaction. I'm mainly confused about the 173 C13 signal which would indicate a C=O bond but the 1666 IR stretch could be indicative of a C=C bond. Anyway, any help would be much appreciated. Thanks!