Ο CH 1202' -1 IR: 1746cm H NMR: a 1.8, m, 2H 2.12, dt, J = 6.7, 7.2 Hz, 2H 2.41,t,J = 7.6Hz, 2H 3.76, s, 3H 4.90, m, 2H f , 5.64, ddt, 6.7, 10.2, 15.1Hz, 1H C7H12O2 IR: 1746 cm-1 1H NMR: a 1.8, m, 2H b 2.12, dt, J = 6.7, 7.2 Hz, 2H C 2.41, t, J = 7.6 Hz, 2H d 3.76, s, 3H e 4.90, m, 2H f 5.64, ddt, J = 6.7, 10.2, 15.1 Hz, 1H

Ο CH 1202' -1 IR: 1746cm H NMR: a 1.8, m, 2H 2.12, dt, J = 6.7, 7.2 Hz, 2H 2.41,t,J = 7.6Hz, 2H 3.76, s, 3H 4.90, m, 2H f , 5.64, ddt, 6.7, 10.2, 15.1Hz, 1H C7H12O2 IR: 1746 cm-1 1H NMR: a 1.8, m, 2H b 2.12, dt, J = 6.7, 7.2 Hz, 2H C 2.41, t, J = 7.6 Hz, 2H d 3.76, s, 3H e 4.90, m, 2H f 5.64, ddt, J = 6.7, 10.2, 15.1 Hz, 1H

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy

Section13.3: The Chemical Shift

Problem 4P: The following 1H NMR peaks were recorded on a spectrometer operating at 200 MHz. Convert each into...

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1. For each set of spectral data, propose an acceptable structure that is consistent with the data. a. MS: M+ m/z=71, IR: 3340, 2960, 2870 cm-1 , 13C NMR: 47.20 (CH2), 25.64 (CH2) ppm b. MS: M+ m/z= 102, IR: 2960, 2870 cm-1, 13C NMR: 72.73 (t), 23.20 (t), 10.80 (q) ppm c. MS: M+ m/z=74, IR: 3310, 2960, 2870 cm^-1, 13C NMR: 62.44 (down), 34.86 (down), 18.98 (down), 13.88 (up) ppm (DEPT-direction) d. MS: M+ m/z=92 (M:M+2=3:1), IR: 2960, 2870 cm^-1, 13C NMR: 67.29 (C), 34.46 (CH3) ppm e. MS:M+ m/z=70, IR: 3070, 2960, 2870, 1666 cm^-1, 13C NMR: 138.92 (t), 114.26 (d), 35.96 (t), 22.17 (t), 13.59 (q) ppm f. MS: M+ m/z= 72, IR: 2960, 2870 cm^-1, 13C NMR: 31.68 (t), 29.80 (d), 22.20 (q), 11.69 (q) ppm g. MS: M+ m/z= 84, IR: 2960, 2870, 1734 cm^-1, 13C NMR: 220.16 (C), 38.30 (CH2), 23.24 (CH2) ppm h. MS:M+ m/z= 138, (M:M+2=1:1), IR: ~3010(broad), 1715 cm^-1, 13C NMR: 173.61(s), 25.21(t) ppm i. MS:M+ m/z=88, IR: 2960, 2870, 1736cm^-1, 13C NMR: 170.95 (C), 60.34 (CH2), 20.98 (CH3), 14.23 (CH3)…