Douglass F. Taber . . . U. of Delaware

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Ordering Information: Organic Chemistry Laboratory: Standard and Microscale Experiments, by Bell, Taber and Clark, third edition, is available from Saunders College Publishing (ISBN 0-03-029272-7).

Examination Copy: For an examination copy of this text, please call (800)237-2665, or contact Saunders College. Be sure to include your name and affiliation and course information.

Overview: We have included several features in this updated text that we have found to work particularly well in the organic laboratory course. These include:

Spectroscopic Problems: As part of the undergraduate organic course, we enjoy using spectroscopic data sets to deduce the structure of organic unknowns. Previously, it has been necessary for the student to purchase a book of spectroscopy tables to participate in such an exercise. For the first time in an undergraduate laboratory text, we have included the necessary data tables. We have also included a graduated set of use-tested problems, as well as detailed instructions at the undergraduate level on how to solve such problems. For the answers to the problems in Chapter 12, Chapter 13 and Chapter 14, see answers. For a typical sample problem, see current problem. The solution to the last problem that we posted can be found under previous problem. We do not use the solving of spectroscopy problems as a one-time experiment, but rather as a continuing activity through the year.

As a service to instructors adopting this text, the authors will provide a set of ten fresh problems at the beginning of each academic year, to be used in examinations.

Note to Instructors: As spectroscopy problems are now included on the MCAT's, it is important that pre-medical students learn how to do them!

New Experiments: This lab manual also includes several new experiments that our students have found to be particularly appealing. In addition to the preparation and crystallization of acetanilide, for instance, we include instructions for the preparation and crystallization of N-acetyl anthranilic acid. This material, which is just as easy to prepare, is both triboluminescent (the crystals flash when ground between two watch glasses!), and strongly fluorescent under UV light.

We have added other experiments that both engage the attention of the student, and that teach new principles. We use PCC, for instance, to oxidize an alcohol to the aldehyde, and flash chromatograpy to purify the product. We reduce the aldehyde back to the alcohol with sodium borohydride. We have also included instructions for chemiluminescence, using the chemistry of the Cyalume light sticks.

Another experiment that we enjoy is based on the preparation of phenyl Grignard. In addition to instructions starting from bromobenzene, we include instructions that start with 4-dimethylamino 1-bromobenzene. The latter Grignard when added to ethyl carbonate gives, after acid hydrolysis, the triphenylmethane dye Crystal Violet. Alternatively, addition of this Grignard to methyl benzoate gives after acid hydrolysis the dye Malachite Green. The graphic at the top of this page represents the sort of design the students enjoy making with these dyes.

Data Report Sheets: With rapidly rising enrollments and limited TA ' s, some instructors have found that it is better to use data report sheets rather than the traditional laboratory notebook. With this system, the TA can handle three sections rather than the traditional two sections. Worksheets are available at Data Report Sheets.

If you have comments or questions about this new organic laboratory textbook, please contact us at Douglass F. Taber