Compounds B and C are isomers with molecular formula C5H9BrO2. The 1H NMR spectrum of compounds B and C are shown below. The IR spectrum corresponding to compound B showed strong absorption bands at 1739, 1225, and 1158 cm-1, while the spectrum corresponding to compound C have strong bands at 1735, 1237, and 1182 cm-1.

Compounds B and C are isomers with molecular formula C5H9BrO2. The 1H NMR spectrum of compounds B and C are shown below. The IR spectrum corresponding to compound B showed strong absorption bands at 1739, 1225, and 1158 cm-1, while the spectrum corresponding to compound C have strong bands at 1735, 1237, and 1182 cm-1.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter18: Ethers And Epoxides; Thiols And Sulfides

Section18.9: Spectroscopy Of Ethers

Problem 18P: The 1H NMR spectrum shown is that of a cyclic ether with the formula C4H8O. Propose a structure.

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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

Compounds B and C are isomers with molecular formula C5H9BrO2. The 1H
NMR spectrum of compounds B and C are shown below. The IR spectrum
corresponding to compound B showed strong absorption bands at 1739, 1225, and 1158 cm-1, while the spectrum corresponding to compound C have strong bands at 1735, 1237, and 1182 cm-1.

1.Based on the information provided, determine the structure of compounds B and C.

2.Assign all peaks in 1H NMR spectrum of compounds B and C.

1H NMR Spectrum of B
doublet
pair bf
iquartéts
triplet
10
2
'H NMR Spectrum of C
triplet
triplet
quartet
triplet
10

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