Question

5. (6) Answer the questions below about the structure that has the followingdata: EA elemental analysis C% = 75.69; H% - 8.80 EA M 206 3430 (broad), 1705 (stron g) 181.4, 140.9, 137.0, 129.5, 127.4, 45.9, 44.1, 30.3, 22.5,18.2 11.9 (broad s, 1H), 7.21 (d, 2H), 7.09 (d, 2H), 3.70 (q, 1H), 2.44 (d, 2H), 1.84 (nonet (9 lines), 1H), 1.49 (d, 3H), 0.89 (d, 6H) S singlet, de doublet, t triplet, q quartet IR 13CNMR 1H NMR a. Determine the molecular formula. Show your work. b. Which proton's signals are split by which protons? Complete the tables below using the NMR data above. Write H1, H2, etc. or "none", as appropriate, in the box provided, and list all protons by which a given proton's signal is split. Split by Proton(s) Split by Proton(s) ppm ppm 2.44 H5 11.9 H1 1.84 7.21 H2 1.49 H7 7.09 НЗ 0.89 н8 3.70 H4 c. Draw all the possible enantiomers and diastereomers of the unknown compound that are consistent with all the data given. 16 H3

Answer 1

fo EA (% - 75.69% , 12. = 8.80% 95.6 % of gas : 156 » No, of carton Atom. = 156=13 88), of 206 = 18 => 18 H'S IR 1705 cm (catborgt group -- Ĉ 3430 uit F-04 of Acid) – dnom za 11.9 ppm (confirmed by 1H-NMR) NMR signals :- 7.21 dl Aromatic Ring with 1,4 7.09 d 1 substitution I group o COOH 1.49 fragments – cnct. , ca- CH - H. C amis 3.70 (9, 1H) 2.44 (d, 24) 1. 84 (nonceut, 14) 1.49 (d, 34) 0.89 (d, 64) MCC-1 (3.7)| $ © i 12.448h2 (1984)CH-CHE CHy-en- momen CH3 | Structures

COOH Protons , и as a 12 Dom split by 1. 9 7. 3) 7, 09 П нЗ 3. По ти? . ча 1, 89 ну из из SH-C-HS (- С - не НЧ 5. и! и h | ня Н 18 Тр. 89 ТН