13. (a) Compound C undergoes a reaction with SOCI2 (or PCI5) to yield compound D (Molecular Formula C10H10OCIB1) which has the following spectral data: Compound D: IR: 1685 cm "; 'H NMR: 8 7.84 (d, J= 8 Hz, 2H), 7.60 (d, J= 8 Hz, 2H), 3.65 (t, J=7 Hz, 2H), 3.18 (t, J = 7 Hz, 2H), 2.25 (pentet, J= 7 Hz, 2H) ppm; "C NMR: d 28, 36, 45, 128, 130, 133, 137, 197 ppm; EI MS m/z: 200, 198(1:1), 185, 183 (1:1). Identify compound C from the spectral data of compound B and justify your observation. %3D

13. (a) Compound C undergoes a reaction with SOCI2 (or PCI5) to yield compound D (Molecular Formula C10H10OCIB1) which has the following spectral data: Compound D: IR: 1685 cm "; 'H NMR: 8 7.84 (d, J= 8 Hz, 2H), 7.60 (d, J= 8 Hz, 2H), 3.65 (t, J=7 Hz, 2H), 3.18 (t, J = 7 Hz, 2H), 2.25 (pentet, J= 7 Hz, 2H) ppm; "C NMR: d 28, 36, 45, 128, 130, 133, 137, 197 ppm; EI MS m/z: 200, 198(1:1), 185, 183 (1:1). Identify compound C from the spectral data of compound B and justify your observation. %3D

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter24: Amines And Heterocycles

Section24.10: Spectroscopy Of Amines

Problem 25P

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