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, i.e., 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 sets 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 derivation 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 realized 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 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.