Intermediate Organic Chemistry

The mission of Intermediate Organic Chemistry is to bridge the gap between introductory Organic Chemistry coursework and advanced/graduate-level coursework but to do so in a way that extends the student-centered approach of most modern introductory Organic Chemistry textbooks. This text makes extensive use of detailed explanations and color coding to facilitate the learning process. The intended student audience is juniors and seniors at the undergraduate level who are taking an Intermediate or Advanced Organic Chemistry class.

This text’s style is one that is shared by many instructors of Organic Chemistry: mechanistically driven and detailed. Extensive use of color coding helps students to learn mechanism and cogently predict reaction products. The electrons that are mechanistically involved in each transformation are color coded. The mechanistic arrows originating from those electrons are colored identically, as are the bonds and/or lone pairs that result from the electron flow. This approach, along with detailed verbal explanations, conveys the narrative of the mechanism.

The text begins with a section on Structure Solving (Part I), which contains chapters on Mass Spectrometry, Nuclear Magnetic Resonance, and Infrared Spectroscopy. A novel feature of this part of the text is a chapter on Structure Elucidation. In this chapter, students engage in a detailed discussion of applying the principles they have learned to actual structure-solving problems. There are six structure elucidation “case studies” that help students to orchestrate fundamental concepts as they approach practical problems.

The text then progresses to Part II: Aromatic Chemistry Expanded. The first chapter in this section discusses the diazotization of aryl amines and the substitution or coupling reactions that follow. The second chapter in this section focuses on aryl halides and their addition-elimination (SNAr) reactions, as well as their elimination-addition (benzyne) reactions.

In Part III (Radical Reactions), students first encounter a chapter on Basic radical chemistry, which is useful since this topic sometimes receives less attention in introductory courses than heterolytic processes. The next chapter in this section is a discussion of Advanced radical chemistry that addresses synthetically useful radical transformations and culminates in an example from the primary literature.

Part IV of the text introduces new ionic reactions through chapters on the synthesis of: alkenes; alcohols; amines; aldehydes, ketones, and their derivatives; and carboxylic acids and their derivatives. The latter four chapters in this five-chapter series also discuss the relevant protecting group chemistry for each functionality. These chapters explore a series of named reactions and/or modern methods for the preparation of commonly occurring functional groups.

Finally, the text concludes with an overview of Polymers in Part V. There is a chapter on chain-growth polymers, which incorporates concepts from the prior section on Radical Chemistry. There is also a chapter on step-growth polymers, which reinforces the topic on Ionic Reactions and culminates with a short introduction to dendrons and dendrimers.

Each chapter includes a set of problems, most of which incorporate compounds or reactions found in the primary chemical literature. Detailed solutions to these problems are found at the end of the text and include the same color-coding approach used throughout the book.