Question

Mass Spectrum (not shown): [M] = 169 (100%) m/z IR Spectrum (not shown): 2985, 2250 (m), 1745 cm1 (all listed are strong (s) unless otherwise indicated) H NMR Spectrum (400 MHz, CDC I3, 25 °C) 5 3 PPM 2H 2H 2H 6H 3H C NMR Spectrum (with DEPT), proton-decoupled (125 MHz, CDCI3, 25 °C) (CH2) (C) (CH3) (CH2) (CH3) (C) (C) (CH2) 180 160 80 140 120 100 PPM 60 40 -20

Please draw the unknown molecule presented in the specs, Thanks!!!

Answer 1

Answer. 1) Mass spectrum - Mto = 169 The odd number mass of moleculoriom te present the presence ols one of odd number of nitrogen atoms in given Compound- 2) IR Spectrums a) 2250cro - IB bond at 2250 CR indicate the presence of -C=N group in Compound: > b) 1745cm IR band at 1745 indicate the presence of ester Carbonyl in given Compound.CR-SOR) . Neglecto, Clotis 3) Molecular kormula Mto represent one of odd number ols Nitrogen IR band at 1745 cron represent estes corbonyl group. Therelore Compound bas two may gen atom HNMR represent presence 15H atoms ond 13 C-NMR represent the presence os g Carbom atoms. The possible formula is m.F - Cg His No2 Deqsee ols Unsaturahcm = (No.ols e+1)- (No. of H) 2 Cg H15 NO2 add ch forn = {c+1) - ) = 11-8 33 Three degree ols unsafercaban tepresent the -CEN & 4) IHNMR spectrum s po(t, 3H) elty Che 1.465, 6H) -&-cth cis 1-8(m, 2H) - Cheche Cthy ?.4 (t, 2H) = CH Che Ethe- 4.4 (S, 2H) 5 -0-cth

5) 13 C-NMR spectrum 8 IT (CH3) 19 (CHF) 21 (elo) two equivalent et 256-6-) 5 quartenary Carbuon 38(-4)=) -= 75 (-(2-) = -cho- 120 (-(EN) 172 (C) R-YO-R On the basis of following spectral data, the possible structure of Compound is 75 25 1465) 17 19 38 cus 12 to fas 1745cm" ge 50cm 1.0(t) 1.s(m) 24t) 44(8) I 1.4(5) 172 172 25