Organic Chemistry as a Second Language: Translating the Basic Concepts is a book that is designed as an aid to students to accompany their lecture text as they progress through the first semester of a two semester sequence of organic chemistry. (A companion text that takes a similar approach and extends to the concepts covered in second semester organic chemistry is planned.) This expertly-crafted 13-chapter book is written in an informal conversational fashion that is eminently readable. Interestingly, the chapters are divided into major principles, or basic concepts, rather than mimicking the subdivisions found in most lecture texts. The chapters include: bond–line drawings, resonance, acid–base reactions, geometry, nomenclature, conformations, configurations, mechanisms, substitution reactions, elimination reactions, addition reactions, predicting products, and synthesis. The chapter treatments de-emphasize memorization and stress common themes that weave from concept to concept. Each chapter is driven by a treatment of the language and the background concepts necessary to understand how to read a problem followed by superb detailed solved problems and then finally an ample array of problems for students to work. Every chapter is efficient, to the point, and replete with excellent problems. The chapters on resonance, acid–base reactions, nomenclature, and geometry are especially excellent, standing out as treatments equal to or exceeding those of any book I have seen.

This book should not be used to replace the lecture textbook. As a supplement it is ideal. However, because of length restrictions imposed by the nature of the work, the scope of topics addressed is not exhaustive. Energy diagrams, aromaticity, and radical chemistry are omitted, for example. The book is meant as a resource for students to acquire the general skills that will enable them to study a typical lecture text more efficiently; basic skills that the author refers to as the “language of organic chemistry.” To that end, Organic Chemistry as a Second Language succeeds in every sense.

The question that remains is whether the students in a real-world context will utilize the book according to its designed intent. Will students struggling to read their lecture textbook really invest the time to read a supplemental text? Seemingly, the only supplemental book students can be counted upon to “read” is the solutions manual that accompanies the lecture text. It can be argued that students often use such solutions manuals to fool themselves into thinking they can solve problems by accessing the solution and working back to the stated problem. Solutions manuals often are more harmful to students than they are helpful. Organic Chemistry as a Second Language is by no means a solutions manual and cannot possibly be used by a student in the unproductive manner just described. Instead Klein’s book is an intuitive training ground for problem solving with detailed problems that can only be used in a forward sense because the problems are structured such that they are accessed step-by-step. Thus, students solving assigned problems from Organic Chemistry as a Second Language will naturally read their way through the text. Assigning problems from this supplemental text rather than (or in addition to) assigning problems from the lecture text would, in this reviewer’s estimation, be dramatically superior in increasing the probability that students will prosper in their organic chemistry course work.

David Klein has provided a supplemental text to accompany first semester organic chemistry that is worthy of the attention of every professional who teaches organic chemistry. The challenge to each of us is to craft a context within which our students will actually use this excellent resource rather than lose it underneath their dorm room bed alongside their ab-crunch machine.