Please show work

1. (13) a. (9) Below is shown the 1H NMR spectrum given by a compound having molecular formula C5H9BrO2.Write the structure of the compound that gave this spectrum in the space given. b. (4) By drawing lines from H's in your structure to the peaks in the spectrum, assign each peak to H's appearing in the structure you drew which would reasonably give rise to that peak. 2. (16) This problem will guide you through the process of predicting the 1H NMR spectrum of the compound drawn below. A table of spectral data can be found at the end of the exam. a. (2) Starting on the left, label each unique 1H environment in the structure with a number or letter. b. (14) Using the labels drawn in part (a) as a guide, predict the 1H NMR spectrum of the compound by completing the data in the table, peak by peak. \begin{tabular}{|l|l|c|} \hline \multicolumn{2}{|c|}{ Characteristic Proton Chemical Shifts } \\ \multicolumn{2}{|c|}{ Chemical shift } \\ Type of Proton \end{tabular} 13 C. NMR Chemical Shift Correlations = proton exchanges with D2O