Provide structures consistent with the following molecular formulae and spectral data, and assign spectral peaks. Write your structures and tables on a sheet of paper. Your structures should include protons (a,b,c,d,etc.) and labeled carbons (1,2,3,4,etc.) as appropriate.

1. Molecular formula: C5H8O

IR (cm-1): 3600 and 3300 cm-1

1H NMR delta: singlets at 1.5,2.2 and 2.9 (broard) ppm in a ratio of 6:1:1.