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4. Answer ALL parts The MS, IR, 1H NMR, 1H{19F} NMR, 13C{1H} NMR, 1H1H COSY, 1H1313C edited HSQC and 1H13C HMBC NMR spectra for an unknown compound with molecular formula C6H5FO are given in the accompanying analytical data booklet. NMR spectra were acquired in DMSO- d6 on an instrument operating at 1H and 13C frequencies of 400 and 100MHz respectively. [1H,100%,I=1/2;19F,100%,I=1/2;13C,1.1%,I=1/2;2H,I=1]. (a) Based on the molecular formula, calculate the index of hydrogen deficiency (IHD), and based on the mass spectrum identify the molecular ion peak and the base peak, reporting their m/z values. (3 marks) (b) Assign the five absorption bands/regions marked on the IR spectrum to specific vibrational modes. Use this information in combination with the IHD to suggest two possible structural features. (7 marks) (c) Explain the presence in the 1H NMR spectrum of the signals at 2.51 and 3.40ppm, and in the 13C{1H} NMR spectrum explain the presence of the group of signals at 39.96ppm, its multiplicity, and the relative intensities of its multiplet components. (4 marks) Question 4 continued on next page Data for Question 4 Mass Spectrum (electron ionization) IR spectrum (condensed phase) 1H NMR Integrals are shown below the main spectrum. Chemical shifts are shown above the 1H{19F} NMR and 1H NMR comparison J-coupling values are shown for the two non-overlapping multiplets. 13C{1H} NMR Chemical shifts are shown above the main spectrum, J-coupling values and labels are shown above the expansions. 1H1H COSY NMR 1H13C edited HSQC NMR [all peaks in this spectrum have the same sign]