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    Monson. R.S. (1971) Advansed Organic Synthesis.

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    Раздел: Химия >>Органическая химия
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    The developments in organic synthesis in recent years have been as dramatic as any that have occurred in laboratory sciences. One need only mention a few terms to understand that chemical systems that did not exist twenty years ago have become as much a part of the repertoire of the synthetic organic chemist as borosilicate glassware. The list of such terms would include the Wittig reaction, enamines, carbenes, hydride reductions, the Birch reduction, hydroboration, and so on. Surprisingly, an introduction to the manipulations of these reaction techniques for the undergraduate or graduate student has failed to materialize, and it is often necessary for students interested in organic synthesis to approach modern synthetic reactions in a haphazard manner.

    The purpose of this text is to provide a survey, and systematic introduction to, the modern techniques of organic synthesis for the advanced undergraduate student or the beginning graduate student. An attempt has been made to acquaint the student with a variety of laboratory techniques as well as to introduce him to chemical reagents that require deftness and care in handling. Experiments have been drawn from the standard literature of organic synthesis including suitable modifications of several of the reliable and useful preparations that have appeared in Organic Synthesis. Other examples have been drawn from the original literature. Where ever possible, the experiments have been adapted to the locker complement commonly found in the advanced synthesis course employing intermediate scale standard taper glassware. Special equipment for the performance of some of the syntheses would include low-pressure hydrogenation apparatus, ultraviolet lamps and reaction vessels, Dry Ice (cold finger) condensers, vacuum sublimation and distillation apparatus, and spectroscopic and chromatographic instruments. In general, an attempt has been made to employ as substrates materials that are available commercially at reasonable cost, although several of the experiments require precursor materials whose preparation is detailed in the text. Some of the reagents are hazardous to handle, but I believe that, under reasonable supervision, advanced students will be able to perform the experiments with safety.

    Introductory discussion of the scope and mechanism of each reaction has been kept to a minimum. Many excellent texts and reviews exist that provide thorough and accurate discussion of the more theoretical aspects of organic synthesis, and the student is referred to these sources and to the original literature frequently. Since it is the purpose of this volume to provide technical procedures, no useful purpose would be served in merely duplicating previously explicated theoretical material.

    The number of experiments that can be done satisfactorily in a one-semester course varies widely with the physical situation and the individual skills of the student. Therefore, no attempt is made to suggest a schedule. I recommend, however, that a common core of about five experiments be assigned. The remainder of the preparations can then be chosen by individual students as dictated by their interests as well as by the availability of chemicals and special equipment. The common experiments, representing frequently used and important techniques, might be chosen from Chapter 1, Sections I and IV; Chapter 2, Section I; Chapter 3, Section I; Chapter 4, Section I; Chapter 5, Section I; Chapter 6, Sections III and IV; Chapter 7, Sections II and VI; Chapter 8, Section II; Chapter 9, Sections I and II; Chapter 11, Sections I and III; or Chapter 13, Section II. Since many of the other experiments draw on the products of this suggested list, the possibility of multistep syntheses also presents itself, and several such sequences are outlined in Appendix 1. Also included, in Appendix 2, are the commercial suppliers of the chemicals required when these chemicals are not routinely available.

    Finally, a brief introduction to the techniques of synthesis is given in Appendix 3. Students with no synthetic experience beyond the first-year organic chemistry course are advised to skim through this section in order to acquaint themselves with some of the apparatus and terminology used in the description of synthetic procedures.


    Monson. R.S. (1971) Advansed Organic Synthesis.

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