Question

Spectroscopy Unknown. The spectra and data provided were obtained from a pure organic molecule. For 1 H NMR Spectra, the integral is given in number of hydrogens (#H) or as a relative ratio. Important coupling constants (J-values) are listed next to the peaks for some examples. For some spectra, an inset (grey box) is also given showing a “zoom-in” on an important part of the spectrum.

Mass Spectrum (not shown): [M] = 169 (100%) m/z IR Spectrum (not shown): 2985, 2250 (m), 1745 cm+ (all listed are strong (s) unless otherwise indicated) 1H NMR Spectrum (400 MHz, CDC13, 25 °C) 2H PPM 2H 2 H 6H 3H 13C NMR Spectrum (with DEPT), proton-decoupled (125 MHz, CDCl3, 25 °C) (C) (CH) (CH2) (C) (CH) (CH2) (CH) 180 .160 140 120 100 80 60 40 20 o PPM

Answer 1

Answer ) Mass spechum- Mt 69 a) The ocd mass ob moleculas im indicate in Compound either One nitrogen or Odcl numbers ob nitsogen atom are present, accocling to the nitrogen tule. 2) TR Spectum b2485c -c- stretching vibrah'on -EN Funcham group fs presentin Compound ester carbonyl group present in Compoune! c) 2250cm 13C NMR Spectsuo 12, 19, 2, 25, 38, 75, 120, '72 Ppm Ihe 13c-NmR show 8 sianal in the spectum Thus Compound have 8 Sets os carbon The Peak at 2 has stiong siqnal Thus it is CrnR Procluceel by to0 equivalent roup The Compouncl have g. Carbom qtoms in its molecala Laommula but fts 3c-Nm R Spectoq show 8-signal This indicute two cacbom are equi valen t 12 C 2 equi valent 22 (steong rč. 25 38 Ch T5 120 T

4Molecular Formulq On the basis os CmR. IR and mass and Ih NM R the possible Losmula os Compound is D.U = 3 The Compound have three degree os Unsakusahřom . This epresent presence os ester carbonyl and -cN group insteuctral oeula ob Cormp oundl 5) IH NmR Spectrum 4 (GH, S) = 1-8 (2H m) си с си2 -си ск 2.4 (2Ht > 4-9 (2H, S) - с,- on the basis os TR, CmR, H NmR the possible Stuctuse ols Compaundd i's 25 22 38 745cm 19 -l-4(s) 75 CH250 cm СИ Си, CH 20 22 .4(s) o(t) 2-4(t) 4.3(s) 72