Chemical Education Today
Book & Media Reviews
Organic Structures from Spectra, 3rd Edition
by L. D. Field, S. Sternhell, and J. R. Kalman
John Wiley and Sons: New York, NY, 2002. xiii + 369 pp.
ISBN 0-470-84362-4 (paperback) $ 40; ISBN 0-470-84361-6
(hardback) $ 99.
reviewed by Alan M. Rosan
The successful analysis of spectroscopic data is surely a
central feature within an undergraduate chemistry program
as it demands a hierarchical ability to discern the structural
import of diverse analytical information. Mastery of this skill
is attained only by exposure to and grappling with a large
number of varied problems. In teaching this material, the
experienced instructor needs to be consciously aware of the
methodology by which solutions are developed, rejected, and
affirmed. The development of such expertise is evolutionary
and requires explicit instruction, continuous reinforcement
and, like the road to Carnegie Hall, ceaseless practice. This
is the goal, ably met, of Organic Structures from Spectra, the
third edition of a classic set of spectroscopy problems. Appearing seven years after the second edition, this updated and
expanded revision is substantially longer (by 149 pages) and
now includes a total of 277 problems, 70 more than previously.
This book is long on spectra and short on descriptive
text and accompanying data. Following a brief but functional five-page introduction there are eight pages on UV,
six on IR, 12 on MS (positive ion E.I.), and 39 on FT NMR.
The text coverage is decidedly not comprehensive (for example IR spectra of alkyl, alkenyl, and alkynyl C–H bonds
and UV spectral intensities are not discussed) and occasionally idiosyncratic, but overall this is a most exciting compilation. I confess that upon receiving it I immediately and
eagerly leapt into the ocean of problems (as much to evaluate their scope and depth as to test my own skills), before
reading all of the accompanying text. I venture that you and
many students will be tempted to do the same and offer that
for the problems alone, this book is a gem. The spectra are
clear and the accompanying writing is lean and crisp. Reflecting the author’s pedagogy, for the most part information is revealed only as it supports structural assignments, that
is, on a need-to-know basis. The sections on 1H NMR spin–
spin coupling and the nine pages on advanced NMR topics,
called Miscellaneous Topics, (dynamic NMR, chirality effects,
NOE, and 2-D techniques) are particularly concise and
sharply focused although I was surprised that, contrary to
modern practice, none of the spectroscopy problems presented utilize any 2-D spectra.
This book was written to accompany a hands-on junior level applied spectroscopy course that emphasizes in-class
problem solving in a seminar format. Some knowledge of
basic spectroscopy is needed and assumed, theory is purposely
kept to a minimum (no discussion of selection rules, no deri-
vation of the N+1 rule, no Karplus plot, etc.), some terms
are used without definition and, save for two worked solutions, examples illustrating the use (and misuse) of data are
not provided. This is decidedly not a how-to-solve-it manual,
a spectroscopy textbook, nor an exhaustive compendium of
spectroscopic tables. It also does not provide a heuristic road
map for problem solving although some general and useful
guidelines are offered in a closing three-page chapter. The
emphasis here is on information connectivity and an awareness of those structural elements that lead to a viable and
unique structure. Its main value lies in the deep level of information evaluation that necessarily accompanies a structure solution to the 277 problems.
The majority of the problems are set in an identical format, showing on one page, IR, MS (with molecular formula
provided), UV, 13C, and 1H NMR (200-600 MHz), all readable and of high quality. NMR spectra often include DEPT
and/or expansions. Providing the molecular formula is, of
course, a big clue and distinguishes these problems from research samples. It also obviates one of the suggested “routine
operations”, that of determining the molecular formula. I
would add that it is also often useful to determine the degree of unsaturation.
Some may find it frustrating that occasionally information that is required to solve, or at least to affirm a structural candidate is not available in the text itself. A strength
of this book is that the problems are quite logically presented
and progressively increase in difficulty (yes, some are quite
challenging). There are many simple(r) problems with a large
number involving benzenoid aromatics. The coverage and
level are appropriate for the beginning student up to the
advanced undergraduate. Another real asset of this text is
that a significant number of problems involve isomers and
congeners with these usually being set together and often
shown on facing pages. I counted 16 problem sets involving isomeric pairs, eight problem sets each involving three
isomers, and one case of the spectra of five structural isomers.
Also included are problems that exemplify complexities arising from chirality, restricted rotation, and equilibrium. Six
problems cite data in prose as it is provided in the literature,
13 specifically require the interpretation of H–H spin–spin
multiplicity and five ask that one draw a schematic representation of the first order multiplicity consistent with a given
set of coupling constants. These latter types of problems are
all too rare and particularly valuable. Examples are varied and
well chosen, being drawn from diverse areas including those
of biological, environmental, industrial, and pharmaceutical
import as well as compounds of a purely structural interest.
My main comment is that one gains not only from the
structural solution (the product) but equally from an awareness of the cognitive pathway by which a solution is developed (the process), which itself necessitates recognizing which
of myriad data is of critical value. This is why spectroscopy
problems are so hard. Being able to solve one does not presuppose an equal facility with the next, a simple algorithmic approach being of limited use. Much value is also real-
JChemEd.chem.wisc.edu • Vol. 79 No. 11 November 2002 • Journal of Chemical Education
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Chemical Education Today
edited by
Jeffrey Kovac
University of Tennessee
Knoxville, TN 37996-1600
ized by a complete NMR interpretation, for example, and I
would suggest that students be required to fully analyze this
and other data. Lastly, I take some exception to the statement expressed in several problems that, referring to a specific spectroscopy, “no significant features were found.” At
times, the absence of evidence is evidence itself.
This compilation naturally invites comparison to other
similar offerings. It provides many more problems but neither as much depth of background nor individual spectral
information (No 2-D, Raman, CD, ORD, CI MS, etc.) as
found in Spectrometric Identification of Organic Compounds
(1997) or Organic Structural Spectroscopy (1998); a principal
competitor may also be WebSpectra, which offers a smaller
array of IR and NMR problems graded by degree of difficulty.
This excellent collection can serve as an instructor’s resource, a stand-alone guide in a spectroscopic analysis course,
or as a supplemental text in physical or organic chemistry. It
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may, in fact, serve many in the latter capacity. While a careful
reading of the book will uncover those inevitable typos
(cystein, ionise, volatilise), slip-ups (the IR doublet for anhydrides is not specified), and omissions (cyclohexanone is not
included on the list of IR functional groups) these are few. I
was more drawn to the direct, utilitarian language, compact
explanations, and the considerable range of problems. Neither literature citations nor answers are provided but a list
of solutions is available from the authors. While it would have
been most helpful to have included an index listing of molecular formulas, the text does provide a short subject index.
As a single integrated resource, Organic Structures from Spectra is to be recommended and will certainly become a staple
of spectroscopic challenges on my shelf.
Alan M. Rosan is in the Department of Chemistry, Drew
University, Madison, NJ 07940; arosan@drew.edu.
Journal of Chemical Education • Vol. 79 No. 11 November 2002 • JChemEd.chem.wisc.edu