Experimental Organic Chemistry: Laboratory Manual

Book Preface

This textbook is designed as a manual to start training students in Organic Chemistry lab work. It also aims to help teachers to find a wide enough variety and complexity of experiments so that they can properly plan the experiences associated with the development of an experimental course and where they can adapt these practices to the required level, time, and resources available at each center. The book seeks to cover the theoretical foundations as well as practical aspects of the discipline. This text includes novel materials such as Green Chemistry and microscale synthesis, without overlooking traditional educational topics such as qualitative organic analysis and some basic principles of structural elucidation by spectroscopic methods.

Organic Chemistry is a highly experimental science based on a body of theory that is consolidated in very basic aspects but at the same time is in constant development. The reactions reflected in any regular publication on Organic Chemistry or theories, principles, postulates, or rules found in the numerous texts dedicated to teaching the discipline are the result of work done by Organic Chemists in the laboratories. Therefore, it is essential for future professionals to acquire a solid background in the laboratory as soon as possible, developing from the outset good habits and skills needed to address the challenges of the experimental work.

From this standpoint, the book is divided into several parts. In the first, safety issues are addressed in the laboratory, both in terms of attitude and responsible behavior and in handling of the chemicals and equipment most frequently used. It also includes some tips for reporting practices and keeping laboratory notebooks, both being critical instruments to accurately reflect the results of the teaching laboratories and/or research.

In the second part, the most common laboratory equipment and the main basic operations that can be undertaken in an Organic Chemistry laboratory are described. Special care has been taken in each case to include tips and warnings that may be useful to students, which we have gleaned as the result of our teaching and research experience. Some of these are too obvious to practitioners of Organic Chemistry but may be of interest to a student starting experimental work in a laboratory. Next, some basic concepts of spectroscopic techniques and how to prepare the corresponding samples for each branch of spectroscopic methods are discussed. This part of the book ends with qualitative organic analysis, which has been included, despite disappearing from some recent texts, because it offers a valuable didactic component, and therefore, we have dedicated a chapter to this item.

One hundred laboratory experiments form the main body of the book. In every experiment a goal, background, and a detailed procedure description are presented. In each case, two types of tables are included: the first one with the basic lab operations necessary for following the procedure, the time needed, and a difficulty code using a flask icon (from one for the simplest to three for the more difficult) and the second one with relevant physical-chemical data and safety information related to the reagents, products, and solvents of every experiment. The experiments are divided into groups, according to the following criteria: In the first group the experiments are designed to provide the basic knowledge of the main techniques of an Organic Chemistry laboratory, the so-called basic laboratory operations. In this case, the reactions or the products involved are secondary concepts. The next group of experiments are constituted by synthetic procedures split on two levels, basic and advanced, according to their complexity, both regarding the reaction type and/or the equipment or procedure necessary.

A second group of experiments is devoted to a full set of microscale and Green Chemistry laboratory experiments. For microscale experiments an introductory chapter includes the description of specific material for this purpose and the basic laboratory operations adapted to it. For Green Chemistry experiments, some of the principles and the basic ideas related to this subject are described. It is important to point out that, to our knowledge, this is the first time that in a general experimental Organic Chemistry text, these types of experiments arepresented. In an up-to-date scientific context, we consider it valuable to offer to the potential undergraduate students a solid foundation on Green Chemistry,not only from a theoretical perspective but also from a practical orientation. We would like to express our appreciation to Garceta Editoral and its staff (our special thanks to Mrs. Isabel Capella) for their facilities that have given us permission to use the copyright of the former Spanish version of the book. Last, but not least, we would like to give our special thanks to Dr. Angel ´ S´anchez-Gonz´alez for the photograph of the front cover and to Mr. David Nesbitt for his invaluable work on the revision of the English manuscript.

This book is dedicated to Dr. Jorge Fidel L´opez Aparicio (b. Osuna, Spain, 1918–2005) graduated in Chemistry at the University of Seville, received the PhD in Oxford, England (1952), and earned a second doctorate at the University of Seville. In 1958 he became full professor of Organic Chemistry at the University of Valladolid, Spain, where he became Dean of the Faculty of Science (1960–1963) and Rector (1963–1965). In 1968 he became full professor of Organic Chemistry at the University of Granada, Spain, a position he held until his retirement in 1986. At the University of Granada he was Dean of the Faculty of Sciences (1971–1974). Among other merits earned were the Grand Cross of Alfonso X the Wise and in 1980 the Gold Medal of the Royal Spanish Society of Chemistry for his research. He was the director of numerous doctoral theses, including those of two of the authors of this book (JIG and FGC-F). He taught that cleanliness, order, observation, rationality, and precision in the preparation of a report, as well as in laboratory work, are vital qualities of a professional in Organic Chemistry. This is our humble contribution in his memory