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  Home > JCE Print > Journal of Chemical Education > Issues > 2000  > December  >
Chemical Education Today
Book and Media Reviews
Interpreting Organic Spectra
by D. Whittaker

reviewed by Charles G. Bass
Department of Chemistry, Wofford College, Spartanburg, SC 29303-3663

Cover
December 2000
Vol. 77 No. 12
p. 1561

Full Text

The Royal Society of Chemistry: Cambridge, UK, 2000. 262 pp. ISBN 0-085404-601-1. $49.00.

Interpreting Organic Spectra is aimed at "A-level students as well as chemistry undergraduates". It is designed to provide a nonmathematical presentation of spectroscopic methods with an emphasis on interpretation. As a result, students using this book will have some understanding of how spectra are obtained, but much more practice in interpreting spectra than is provided by many other texts on the subject. The techniques covered include infrared spectroscopy, mass spectrometry, ultraviolet spectroscopy, and both carbon and proton NMR spectroscopy. Each technique is covered separately in its own chapter and subsequently used in combination with the other techniques to provide more detail regarding the structure of unknowns.

The strength of infrared spectroscopy is in the determination of functional groups. This point comes across loud and clear in the first chapter. No discussion is included on how the technique may be used to determine such things as the substitution pattern of simple aromatics from overtone patterns or how to tell if an alcohol is primary, secondary, or tertiary. It seems that a reference to tables where one can find such information might be appropriate.

Mass spectrometry is covered next. I found this section and all the mass spectra that follow to need some work. It was pointed out that the number of carbons in a compound could be determined by comparing the relative size of significant peaks with those of one mass unit larger. This is valuable information. A useful addition to these spectra would be the inclusion of a table with the relative abundance data. I also found the font size used on these spectra to be too small. If a problem is rushed through it becomes very easy to read a mass of 120 as 128. This would certainly influence the interpretation of the problem. Good discussion is provided on how to determine if a halogen is present and on interpreting the McLafferty rearrangement. A reference to where the reader may find more extensive mass tables like those found in works such as Spectrometric Identification of Organic Compounds, 6th ed., by Silverstein and Webber would also strengthen this chapter.

The fifth chapter is on 13C NMR spectroscopy and is very well done. Good explanations are provided for the observance of small carbonyl signals and why DEPT (Distortionless Enhancement by Polarization Transfer) spectra are important. The author also points out that the technique is not good at determining whether a double bond is cis or trans, but that proton NMR can be used in that instance. A minor improvement might be a reference to page 152, where coupling constants for cis and trans isomers may be found. Another solved problem shows that in certain instances "we cannot always tell which carbon atom is next to which". It is also stated that the "problem can be solved by 1H NMR". It would help to revisit the same problem in the chapter on 1H NMR and demonstrate how.

Chapter 9 deals with 1H NMR. Chemical shift, integration, coupling patterns, coupling constants, and exchange of acidic protons by deuterium are discussed. The problems are good except for the same print quality and font size (particularly with integration) issues. One annoyance is that in some problems protons attached to nitrogen or oxygen are clearly shown in the spectrum and indicated as "disappearing on D2O shake", whereas in other problems these protons are not displayed.

The chapters dealing with combining techniques could be improved by including one example problem worked out in detail. It should also be pointed out that there are no problems that include COSY, HETCOR, or other 2-dimensional NMR experiments.

The premise of the book is a good one. The determination of structures by spectroscopic methods is best done by practice. One hundred and sixty-five problems are provided in 13 chapters. Answers are given in the back of the book, but no explanation is given for how these answers may be derived from the spectra. This book will certainly give the reader a great deal of practice in interpreting spectra, but could be improved by better print quality (particularly for mass spectra), detailed solutions, and references to more detailed tables.

More Information
*  Citation
Bass, Charles G. J. Chem. Educ. 2000 77 1561.
*  Keywords
Organic Chemistry
*  History
Created:
Last Updated:
November 3, 2000
April 15, 2005
  Home > JCE Print > Journal of Chemical Education > Issues > 2000  > December  > Page 1561


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