ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
9th Edition
ISBN: 9780134645704
Author: WADE AND SIMEK
Publisher: PEARSON
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Chapter 12, Problem 12.22SP
Interpretation Introduction

Interpretation: The trends in abundance of the molecular ions and the ions at mass 57 and the intensities of the peaks of the mass spectrums of noctane, 3,4dimethylhexane and 2,2,3,3tetramethylbutane are to be predicted.

Concept introduction: Mass spectroscopy provides a reliable molecular weight for an unknown compound and also gives us the information about the molecular formula as well.

Fragmentation gives the resonance stabilized cations whenever possible. Loss of a small molecule is usually indicated by a fragment peak having an even mass number corresponding to loss of an even mass number.

To determine: The trends in abundance of the molecular ions and the ions at mass 57 and the intensities of the peaks of the mass spectrums of noctane, 3,4dimethylhexane and 2,2,3,3tetramethylbutane.

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The mass spectrum of n-octane shows a prominent molecular ion peak (m>z 114). There is also a large peak at m>z 57,but it is not the base peak. The mass spectrum of 3,4-dimethylhexane shows a smaller molecular ion, and the peak atmass 57 is the base peak. Explain these trends in abundance of the molecular ions and the ions at mass 57, and predict theintensities of the peaks at masses 57 and 114 in the spectrum of 2,2,3,3-tetramethylbutane.1
The mass spectrum of 2,2-dimethylpropane shows only a very weak molecular ion peak at m/z = 72. However, a large peak at m/z = 57 is seen. Suggest a possible structure of the fragment giving rise to this large peak and suggest a reason as to why this peak is so large.
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