Microscale Organic Laboratory: With Multistep and Multiscale Syntheses 5th Edition
Twenty-five years ago, in 1985, when Microscale Organic Laboratory (MOL) was first published (as paperback Xerox copies of an unproofed manuscript!), it was the only microscale organic laboratory text available. In the February 1999 Book Buyers Guide Supplement to the Journal of Chemical Education, however, there were seventeen laboratory manuals (of a total of thirty-nine) containing miniaturized, fully microscale, or a mixture of micro and macro experiments. Fast forward ten years and without any doubt, microscale techniques have solidly established their place in chemical education. The number of lab manuals currently in print reflects the growing number of students being introduced to organic chemistry through microscale techniques. While the conversion may not yet be quite as high as the eighty percent predicted by David Brooks back in 1985, a conservative estimate would be that a solid two-thirds majority of sophomore students now work with miniaturized experiments compared with the amounts of material employed in these laboratories in the late 1970s.
The major changes that were made to MOL in the fourth edition were very well received by our readers. Indeed, we are now nearing the fine-tuning stage in the evolution of this laboratory text. Hence,MOL5 on the surface will look very much like MOL4. MOL5, however, has undergone further significant internal reorganization and rewriting. Many helpful suggestions have been received from reviewers and from instructors who have used previous editions of this text. As a result, some major changes have been made for this new edition:
• A key change to the 5th edition is the modification of the procedural sections to allow for inquiry-based experimentation. Reaction times have been replaced with guidelines, and options on how to best monitor reactions and gauge product purity are left to the discretion of the student or instructor. Many ideas and new approaches can stem from this change— for example, instructional sections can be split into small groups and each group can approach the monitoring of a reaction differently. Using a completely separate set of experiments, discussions can be pursued which focus on reaction purity and evidence which offers the experimentalist sufficient data about what was prepared. Students can then compare notes at the end of the lab period and discuss the various approaches and end results.We hope that this change will allow the lab to become a more interactive experience between groups of students, should that be the wish of the instructor. The opportunity to monitor a reaction rather than assume reaction completion by simply following a time-based instruction and to allow for students to gather additional evidence of product purity empowers the student and adds an element of excitement to the lab experience. Optional inquiry-based guidelines have been added to experiments 5A, 5B, 7, 19B, 24A, and 32. Experiments 11A, 16, and 28 have been modified in a way which focuses on validation of product purity. References to inquiry-based guidelines and validation experiences are noted in the text.
• The use of microwave heating as a tool in synthetic organic chemistry is fast-growing and is becoming an enabling technology. Optional instructions have been added to experiments to allow for the integration of microwave heating as a tool for performing reactions. Since reaction times are shorter than when conventional heating methods are used, students have the opportunity to supplement these activities with traditional techniques and as stated above engage in discussions comparing the two. Optional microwave heating instructions have been added to experiments 7, 8, 15, 22, and 30. References to microwave use are noted in the text by the use of this icon .
• A rich collection of end of chapter exercises and the addition of pre and post lab questions provides students with the valuable opportunity to test and practice their own understanding of each laboratory experiment.
• Discussion sections that appear at the beginning of each Experiment have been added, revised, and expanded upon. These discussion sections provide chemical context/background for each experiment, and provide more information regarding the chemical principles involved in each experimental procedure.
• The Refractive Index material, which was formally in chapter 4, has been moved to the book companion web site: http://www.wiley.com/ college/mayo.
• Chapter 10W, “Advanced Microscale Organic Laboratory Experiments,” (formerly chapter 7) has been moved to the book companion web site: http://www.wiley.com/college/mayo. Additional Resources Text web site-http://www.wiley.com/college/mayo As with the previous edition, a major portion of the background theoretical discussions have been moved to the text web site, without affecting the operational part of the text. Likewise, the web site has allowed us to move a number of more advanced discussions out of the printed text. Wherever the shift of this material has occurred the move is flagged by reference call-outs using an icon .
These web reference discussions include information on the following topics:
• Microscale lab equipment and techniques
• Semimicroscale distillation
• Reduced pressure distillations with microspinning band columns
• Vacuum pumps and pressure regulation
• Measurement of Specific Rotation
• Introduction to Infrared Spectroscopy—Introduction to Theory
• Group Frequencies of the Hydrocarbons
• Characteristic Frequencies of the Heteroatom Functional Groups
• Instrumentation—the Infrared Interferometer
• Tables of Derivatives
The majority of the background infrared spectra and the associated discussions used to develop the use of group frequencies from these spectra are also found on the web site, while the text still contains the essential tables of characteristic frequencies that are in every day use in the laboratory. The many compound data tables, used primarily in the chapter on qualitative identification, also reside on the web site. The Classification of Experiments Based on Mechanism is also available on the web site.
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