Laboratory Techniques in Organic Chemistry
Laboratory Techniques in Organic Chemistry
4th Edition
ISBN: 9781464134227
Author: Jerry R. Mohrig, David Alberg, Gretchen Hofmeister, Paul F. Schatz, Christina Noring Hammond
Publisher: W. H. Freeman
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Chapter 24, Problem 5Q
Interpretation Introduction

Interpretation:

The fragmentation that leads to a peak at m/z of 127,125 and 105 should be determined.

Concept introduction:

Mass spectrometry is an important spectroscopic method to determine the molecular weights and molecular formulas of the compounds. It also can help in the identification of compound or determination of its structure.

A mass spectrograph is plotted between the intensity of ions on y-axis and m/z on x axis. Mass spectrometry works as follows:

  • A sample is converted into a gaseous ion by an ionization technique in the mass spectrometer.
  • Then on the basis of mass-to-charge (m/z) ratios, gaseous ions are arranged.
  • These ions generate electric current at detector and a mass spectrum is formed.

To assign the molecular weights to compounds the rule of thirteen is utilized in mass spectrometry. Thirteen here is obtained by the addition of the mass of carbon and hydrogen.

If the molecular ion peak is intense then M+1 and M+2 the peak will also be observed. The ratio of intensities of M+1 and M+2 predict the existence of halogen isotopes. If the ratio of M+1 and M+2 peak is 1:1 then bromine isotopes are present in the mixture and if 1:3 is the intensity ratio then the presence of chloride isotope is confirmed.

The peak intensity ratio depends on the abundance of isotopes in nature.

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Please answer the question and provide a detailed drawing of the structure. If there will not be a new C – C bond, then the box under the drawing area will be checked.  Will the following reaction make a molecule with a new C – C bond as its major product:  Draw the major organic product or products, if the reaction will work. Be sure you use wedge and dash bonds if necessary, for example to distinguish between major products with different stereochemistry.
Please do not use AI.  AI cannot "see" the molecules properly, and it therefore gives the wrong answer while giving incorrect descriptions of the visual images we're looking at.  All of these compounds would be produced (I think).  In my book, I don't see any rules about yield in this case, like explaining that one product would be present in less yield for this reason or that reason.  Please explain why some of these produce less yield than others.
Please answer the question and provide detailed explanations.
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