Reviews of Workbook for Organic Chemistry: Supplemental Problems and Solutions and Physical Organic Chemistry: A Guided Inquiry Workbook

Abstract

I this review, I consider supplemental course materials Workbook for Organic Chemistry: Supplemental Problems and Solutions by Jerry Jenkins and Physical Organic Chemistry: A Guided Inquiry Workbook by Kelly Butler. As the organic workbook is for undergraduates and the physical organic workbook is for advanced undergraduates and graduate students, I will begin with the organic workbook. Quite simply, for students (and instructors) seeking additional problems to supplement a traditional undergraduate organic course, Jenkins’s workbook is superb. The paper format provides students plenty of opportunity to draw molecules while solving problems. For instructors interested in online homework, W. H. Freeman has also placed these problems in WebAssign. Nearly all current organic texts contain an assortment of problems for students to solve. Virtually all of these texts provide a supplemental “solutions manual” of worked solutions to the text problems. In addition, many texts supplement the traditional paper problems and solutions manuals with online problems, often with learning “hints” and guided solutions. So one might then question the need for additional problems as presented in Jenkins’s workbook. As Jenkins writes in his preface, “[B]etter performing students, however, consistently ask for additional exercises. It is the purpose of this manual, then, to provide Supplemental Problems and Solutions that reinforce and extend those textbook exercises.” Jenkins has succeeded in this task of providing additional problems; most are suited for better performing students. The workbook is organized in two parts: problems and solutions to problems. The problem chapters are arranged by functional group, following the sequence of most organic texts by beginning with alkanes and ending with amines. Each functional group chapter is presented in a standard format of general information followed by reactions, syntheses, and mechanisms. The reaction sections present problems in the form of reactant(s), reagent(s), and students then draw the product(s). The syntheses sections present starting and product molecules and students then provide a sequence of reagent(s) and intermediate product(s) to afford the transformation. The mechanism sections present reactant(s), reagent(s), and product(s) and direct students to outline a detailed step-by-step mechanism using electron-pushing arrow formalism. In addition to the functional group chapters, there are chapters on basics (hybridization, formulas, physical properties, acids and bases, resonance), stereochemistry and NMR (proton only). The preface also includes TIPS (To Improve Problem Solving) on mechanism arrows, equilibrium versus resonance arrows, hydrogen nomenclature, state of association and dissociation, and a listing of common abbreviations introductory students are likely to encounter. The solution chapters mirror the format of the problem chapters and provide straightforward and detailed solutions for each problem in the problem chapters. Some of the solutions also provide explanatory notes. While Jenkins’s workbook is successful in providing additional problems for better performing students, the target audience could be expanded to include “poorer performing students” with only slight adjustments. The poorer performing students are often the least motivated to work “supplemental” problems, but perhaps are the most in need of supplemental work. Because the workbook solutions contain minimal explanatory notes, and the synthesis solutions none at all, poorer students are likely to find the problems frustrating for lack of explanation to help them along and as a result, not use them at all. More detailed explanatory notes might help develop the chemical insight poorer students often lack, enabling them to at least get started on the problems rather than giving up for not knowing where to begin. For example, in the syntheses sections before presenting the solution, the author might provide some analysis of the functional groups and their arrangement in the synthetic target versus the starting molecule, along with short explanatory notes on how the various transformations and arrangements may be achieved, then present a solution to the problem. Aside from this shortcoming, the workbook provides plenty of problem-solving practice in all the topics undergraduates are likely to undertake in their organic course sequence, and for this, the workbook is a valuable contribution. As Butler writes in the author’s notes, Physical Organic Chemistry: A Guided Inquiry Workbook is “intended for use in an introductory graduate or an advanced undergraduate physical organic chemistry course in conjunction with a textbook.” The workbook is written using the process-oriented, guided-inquiry learning (POGIL) approach by providing activities for students working in small, self-managed groups. The success of the POGIL approach for courses in general and organic chemistry is well documented. A quick review of the literature indicates sparse POGIL use in graduate-level and upper-level undergraduate chemistry courses. While many upper-level courses employ small