Question

4. In Chapter 18 we will learn about the electrophilic aromatic substitution reaction shown below. structure of the product of the reaction based on the data given below Predict the Br2 AlBr3 Product Molecular Formula: CH1302Br Calculate the units of unsaturation-(2C+ N + 2-X-H)/2 where X is any halogen. 13C NMR (ppm): 9.7, 19.9,29.5, 73.6,123.0, 128.9, 129.6,132.0, 132.3,135.9,165.9 List at least one thing you can learn from the 13C NMR data Indicate the functional group and specific bond that each peak represents R (cm 3054, 2908, 1731, 1598, 1502 H NMR sextet pentet PPM Draw the molecule responsible for all of the data above. Assign unique hydrogens (A-Z). Label the spectrum to indicate which unique hydrogen(s) are responsible for each peak in the 1H NMR

Answer 1

Molecular formula of P dt C_11 H_13 O_2 Br: unit of unsaturation = 2 times 11 + 2 - 1 - 13/2 = 22 + 2 - 14/2 = 10/2 = 5 From 13_C HMR: The peak at 165.9 ppm indicates the presence of ester carbonyl C = 0 From IR data: The peaks at 3054 and 2908 cm^-1 represents the presence of SP^3 C-H stretching. The peak at 1731 cm^-1 is due C = 0 stretching of ester group. This indicates presence of -CO_2 R group. The peaks at 1598 cm^-1 and 1502 is due to benzene ring. From 1HNMR data, the structure of molecule is Br_2 and AlBr_3 generates Br^+ insitu which goes to meta position because ester group is meta directing group.