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Propose a structure consistent with each of the spectral data:

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter12: Structure Determination: Mass Spectrometry And Infrared Spectroscopy

Section12.SE: Something Extra

Problem 48AP: The infrared spectrum of the compound with the mass spectrum shown below lacks any significant...

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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

Answer for both:

1) Propose a structure consistent with each of the spectral data:

C5H10O: IR peak at 1740 cm-1
NMR (ppm): 1.15 (triplet, 3H), 2.30 (quartet, 2H), 1.25 (triplet, 3H), 4.72 (quartet, 2H

2) Propose a structure for compound Z, which has the following spectroscopic properties

MS: M+ = 88
IR: 3300 cm-1
1H NMR: 0.85 d (6H doublet); 1.40 d (1H multiplet); 2.68 d (2H quartet); 3.55 d (2H triplet)
Broadband decoupled 13C NMR: 322.7, 25.0, 41.8, 60.5 d
DEPT-90: 25ppm
DEPT-135 positive peaks at 19 ppm, 25ppm, negative peaks at 41.8, 60.5 d

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