An unknown compound produces an 1H NMR spectrum with only three signals: 1.8, 2.8, 7.5 (broad) ppm, all singlets that integrate in a 6:3:1 ratio, respectively. The 13C NMR spectrum shows 4 signals. Both spectra are provided below. The mass spectrum shows a molecular ion region with the following peaks: m/z 135 (100%), 136 (5.9%), 137 (33%). Determine the number of carbons, molecular formula, and propose a structure. Assign all 1H and 13C NMR signals to specific chemical environments or specific hydrogens in your structure.

An unknown compound produces an 1H NMR spectrum with only three signals: 1.8, 2.8, 7.5 (broad) ppm, all singlets that integrate in a 6:3:1 ratio, respectively. The 13C NMR spectrum shows 4 signals. Both spectra are provided below. The mass spectrum shows a molecular ion region with the following peaks: m/z 135 (100%), 136 (5.9%), 137 (33%). Determine the number of carbons, molecular formula, and propose a structure. Assign all 1H and 13C NMR signals to specific chemical environments or specific hydrogens in your structure.

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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