Question

3. Provide structures consistent with the following spectroscopic data: (18) COMPOUND ONE: CuH12O2 9--442 131 3063 103 2982 1714 176 1639 148 0 50 75 100 125 150 175 000 166.8 0H 7.67 (1H, d, J 15.8 Hz) 7.28-7.57 (5 H, doublets and triplets, J 8 Hz) 6.43 (1H, d, J 15.8 Hz) 4.24 (2H, q, J 7.1 Hz) 1.32 (2H, t,J 7.1 Hz) 144.5 1H 134.5 0H 130.2 1H 128.9 2C 1H@ 128.1 2C 1H@ 118.4 1H 60.4 2H 14.3 3H 00 180 160 140 120 100 80 60 40 20 0 11 10 9 8 7 6 5 4 3 1. 0 -N 77

Answer 1

calculation of for 9, Hipog: Double bond equalent (DBE) ) for a .en Hento- saturated Hydrogen 8 = 24H C n=11 cu 424 Molecular formula Hydrogens = 12H toric e saturated Hydrogens - Molecular formula Hydrogens = E4H - 12H = ( 4 Double bonds + Iring + IC=0) OBE =66

based on H NMR H. C = Data The proposed structure is e-o-che-CH3 It consists of 5 Types of - protons (a, b, c, d, e) - Trans-Ethyl cinnainate It is trans llorer based on. J Valve (coupling const I value for trans Isomer Z 16 H2, In the given Data J = 15.8 HZ (odh . -o- CHg_CH 5 Ely re

> IR Data: an absorption band at 1714 cl are to y=0 Stretching 4 3063 cal ch stretching in Aromatic syster. 9. 1639 Ch Cac stretching in at +2982 .cr . =ch stretching in alkene alkene. Mass Data: ll CHECH-C-0-67 toev. -CH=CH-C-0 Holecular com h 12 = 176 = 176 4-Croft HẨck- SCHICHE - CH2 - CH2) by = 131(berse peak)

QOX y co NMR: 9 signals H. (e) by c-o-CH2 - CH2 CECC) y la (045)C,d,e, t, 9, h, i) P t 6 (al Type S value: M. 3 ppi (34) h b + Type & value: 60.4 PPET(27). di type s vare: 118.4 PPM (1H) (C) type: 166.8 PPD Tel + Type S value: 144.5 PPM ili (f) Type & vake: 134.5ppri Coty . alt=P pn C(M) {с Cool Type & value. Toeg (h) Type & value: 128:1 (2c, nt) 1 y Type & vale: 130-2 PM (PH)

Type of Proton l Integration I Multiplicity (nt I s Vakce (ppry fa) 3H Triplet quatret ZH 개 doubler (13A PPn. 4624 ppry 7 SPM (J= 15.8 H2) 7.67 PPM (J=15082) 137 - 7.5 Ph. doublet oloubiet, niplet Higher & value than He. - Hd proton has due to Resonance. H(d) su oft K CH-CH Zc-oft ph a the proton present on Low Electron density Region, Higher & value