1st Edition

Advanced Organic Synthesis A Laboratory Manual

By Dmitry V. Liskin, Penny Chaloner Copyright 2016
    132 Pages 63 B/W Illustrations
    by CRC Press

    132 Pages
    by CRC Press

    Laboratory experience equips students with techniques that are necessary for professional practice. Advanced Organic Synthesis: A Laboratory Manual focuses on a mechanistic background of key reactions in organic chemistry, gives insight into well-established trends, and introduces new developments in the field.

    The book features experiments performed by primary author Dmitry Liskin while he was a graduate student, providing a real-life quality to the experiments by using examples that have actually been conducted. It also includes recent experiments that have been published in peer-reviewed journals. The experiments are presented in a brief and simple manner, including bulleted lists of the required materials and equipment as well as step-by-step walkthroughs. Each experiment also carefully details safety issues and waste disposal methods.

    Emphasizing techniques and approaches used in more advanced labs, Advanced Organic Synthesis: A Laboratory Manual gives undergraduates the theoretical knowledge and practical experience they need to succeed at more advanced levels of research involving organic synthesis at the graduate or industrial level.

    Diastereoselective Reduction of Estrone
    Equipment Required
    Materials Required
    Overall Reaction
    Procedure
    References

    Synthesis of 2,2-Dimethyl-4-pentene-1-amine
    Equipment Required
    Materials Required
    Overall Reaction
    Procedure
    References

    Protection of 2,2-Dimethyl-4-pentene-1-amine
    Equipment Required
    Materials Required
    Overall Reaction
    Procedure
    References

    Optimization of the Reaction Conditions for the Aminofluorination of N-(2,2-Dimethylpent-4-enyl)-2-toluenesulfonamide
    Equipment Required
    Materials Required
    Procedure
    References

    Asymmetric Robinson Annulation
    Equipment Required
    Materials Required
    Overall Reaction
    Procedure
    References

    Formation of N-Benzylcinchonidinium Chloride from Cinchonidine
    Equipment Required
    Materials Required
    Overall Reaction
    Procedure

    Chiral Resolution of BINOL (1,1’-bi-2-Naphthol) with N-Benzylcinchonidinium Chloride
    Equipment Required
    Materials Required
    Overall Reaction
    Procedure
    References

    Transesterification of Phosphatidylcholine and FAME Quantification
    Equipment Required
    Materials Required
    Overall Reaction
    Procedure
    References

    Green Chemistry: Solventless Sequential Aldol and Michael Reactions in the Synthesis of Kröhnke Pyridine
    Equipment Required
    Materials Required
    Overall Reaction
    Procedure
    References

    Carbonyl Chemistry in a Multistep Synthesis
    Equipment Required
    Materials Required
    Overall Reaction
    Procedure
    References

    Multistep Synthesis of a Bioactive Peptidomimetic
    Equipment Required
    Materials Required
    Stock Solutions
    Overall Reaction
    Procedure
    References

    Total Synthesis of a Natural Product: Caffeic Acid Phenethyl Ester (CAPE)
    Equipment Required
    Materials Required
    Overall Reaction
    Procedure
    References

    Appendix: Essential Laboratory Techniques
    Choosing Glassware
    Drying Glassware
    Purging with Inert Gas
    Setting a Pressure Release Valve
    Handling of Pyrophoric and Water-Sensitive Reagents
    Setting Up a Chromatography Column
    Pulling Spotters
    Spotting and Running a TLC Plate
    Dry Solvents and Reagents
    Setting Up an Apparatus

    Biography

    Dmitry V. Liskin , PhD, is a lecturer at Christopher Newport University, Newport News, Virginia. He graduated with a degree in ACS biochemistry from Mississippi College, Clinton, Mississippi. As an undergraduate, he worked on the synthesis and characterization of pseudoacids under the mentorship of Dr. Edward Valente. He moved to Seattle, Washington, for his doctorate studies in organic chemistry at the University of Washington. He joined a research group of Dr. Forrest Michael and developed alkene difunctionalizations as novel routes to substituted nitrogen heterocycles, mainly focusing on the use of hypervalent iodine oxidants. Penny Chaloner , PhD, completed her undergraduate and graduate studies in Cambridge and had postdoctoral fellowships in Oxford, followed by a period in the United States as an assistant professor at Rutgers University and teaching at Harvard Summer School. She returned from the United States to a permanent position in Sussex, from which she recently retired. She first taught organic sophomore chemistry at Harvard in 1981 and has taught some version of this either once or twice a year ever since. Some of that was in North America, much in the United Kingdom, at Sussex, where for many years she taught the American organic chemistry sequence to visiting students, and to a large group of international premeds. Penny Chaloner has experience teaching this sequence in groups sized from two to almost a thousand.