Question 4: In the reaction below the separation of the mixture of diastereomeric lactone products was difficult and therefore the mixture shows the 'H NMR spectrum (300 MHz) in CDC13, from both diestereomers. Please indicate which resonances go with which diastereomer? Please explain your basis of determination from the given NMR spectrum. Also, what was the diastereomeric ratio of the major and minor isomers in dr? Please draw the diastereoisomer and list the chemical shifts of the key 1H-NMR resonances affiliated with it. Explain the reason. [you can use coupling constant and Karplus equation to elucidate, Also the close-up 'H NMR spectra with 300 MHz in CDC13 shown in figure might be convenient for this elucidation.] 0.11 "J- 8.5 cosa -0,28 for O SS 90 9,5 cosa -0.28 for 90 S S 180 0.10 0.09 CsH11 0.08 OH Tsi pyridine CH, ROP 4.1912-4.1839 4.1815 4.1607 L 1705 2047 6.1473 HO 0.07 OH CH, CH, 0.05 0.05 0.04 0.03 14.5356 0.02 0.01 . 0.22 1.01 4.70 4.65 4.60 4.55 4.45 4.30 4.25 4.20 4.15 4.10 4.05 4.00 440 4.35 Chemical St Opm) (2)