15. Compound A, a hydrocarbon with M* = 96 in its mass spectrum, has the ¹³C spectral data given below. On reaction with BH3 followed by treatment with basic H₂O2, A is converted into compound B, whose ¹³℃ spectral data are also given below. Propose structures for A and B. Compound A Broadband-decoupled ¹³C NMR: 26.8; 28.7; 35.7; 106.9; 149.7 8 DEPT-90: no peaks DEPT-135: no positive peaks; negative peaks at: 26.8; 28.7; 35.7; 106.9 8 Compound B Broadband-decoupled ¹³C NMR: 26.1; 26.9; 29.9; 40.5; 68.2 8 DEPT-90: 40.5 8 DEPT-135: positive peaks at 40.5 8; negative peaks at: 26.1; 26.9; 29.9; 68.2 8

15. Compound A, a hydrocarbon with M* = 96 in its mass spectrum, has the ¹³C spectral data given below. On reaction with BH3 followed by treatment with basic H₂O2, A is converted into compound B, whose ¹³℃ spectral data are also given below. Propose structures for A and B. Compound A Broadband-decoupled ¹³C NMR: 26.8; 28.7; 35.7; 106.9; 149.7 8 DEPT-90: no peaks DEPT-135: no positive peaks; negative peaks at: 26.8; 28.7; 35.7; 106.9 8 Compound B Broadband-decoupled ¹³C NMR: 26.1; 26.9; 29.9; 40.5; 68.2 8 DEPT-90: 40.5 8 DEPT-135: positive peaks at 40.5 8; negative peaks at: 26.1; 26.9; 29.9; 68.2 8

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Concept explainers

NMR Spectroscopy

NMR stands for Nuclear Magnetic Resonance in which the study of different molecules is done based on the interaction of radiofrequency electromagnetic radiations with the nuclei of molecules placed in a strong magnetic field. A precise study of spectra of visible light and all bands of electromagnetic radiation is called spectroscopy.

Question

15. Compound A, a hydrocarbon with M* = 96 in its mass spectrum, has the ¹³C spectral data given
below. On reaction with BH3 followed by treatment with basic H₂O2, A is converted into
compound B, whose ¹³C spectral data are also given below. Propose structures for A and B.
Compound A
Broadband-decoupled ¹³C NMR: 26.8; 28.7; 35.7; 106.9; 149.7 8
DEPT-90: no peaks
DEPT 135: no positive peaks; negative peaks at: 26.8; 28.7; 35.7; 106.9 8
Compound B
Broadband-decoupled ¹³C NMR: 26.1; 26.9; 29.9; 40.5; 68.2 8
DEPT-90: 40.5 8
DEPT-135: positive peaks at 40.5 8; negative peaks at: 26.1; 26.9; 29.9; 68.2 8

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