4. (22 Points) The IR spectrum and proton NMR spectrum for a compound with molecular formula C,HO is given below. IR Spectrum this 4000 3000 2000 1600 1200 800 v (om) persion soale H NMR Spectrum (400 M CDO, on expansons 1o es om 10 6. 3. 8 (ppm) a. How many unsaturations are in the compound? b. What functional group is responsible for the 1715 cm in the IR? c. Fill in the following table to assign the proton NMR spectrum. Circle the hydrogens in each structural fragment you place in the Proton Interpretation box that are responsible for the chemical shift. #H J. Hz Proton Interpretation 8, ppm 0.98 6. 2.21 m 2.31 2. 9.75 a. Put the structure of unknown CH0 in the following box.