Organic Structure Analysis » (2nd Edition)

all in the Department of Chemistry at University of California, Santa Cruz

Organic Structure Analysis is an ideal text for upper-level undergraduate and first-year graduate courses in organic spectroscopy. It provides students with the background necessary to effectively apply spectroscopic data in establishing features of molecular structure. Unique in its coverage, it is the only text that emphasizes strategies, interpretation, modern techniques, and problem solving. The text's major aim is to show how spectra can be efficiently examined in order to identify a molecule's major structural elements. It focuses on four techniques which are used on a day-to-day basis by most organic chemists: nuclear magnetic resonance (NMR), mass spectroscopy (MS), infrared (IR), and ultraviolet-visible (UV-VIS). Each chapter provides different perspectives on using spectroscopic data in a step-by-step process to establish structural features such as an overall carbon framework; the presence and location of functional groups; the regiochemistry and stereochemistry of substituents; and, finally, the absolute stereochemistry of chiral centers. Recent advances in NMR and MS have changed the way these components are introduced and used in organic spectroscopy courses. Unlike similar texts, this book provides ample, up-to-date coverage of the latest developments in NMR and MS techniques.
Organic Structure Analysis adopts a practical approach to the subject which emphasizes building experience; the authors recognize that a combination of problem solving, access to data from models, and understanding the rules of spectral interpretation helps students to build expertise in structure determination from spectra. It outlines elements of theory, but with an emphasis on those directly relevant to spectral interpretation. The text is divided into three major sections; the first section provides extensive coverage of each of the individual methods, the second section illustrates how the strategies of organic structure are actually applied in ten problems whose solutions are provided, and the third section consists of fifty unsolved problems which range from simple monofunctional compounds to complex natural products.

Ch. 1 Using Spectroscopic and Analytical Data in Organic Structure Analysis

Ch. 2 Introduction to Nuclear Magnetic Resonance

Ch. 3 Interpretation and Use of Proton and Carbon Chemical Shifts

Ch. 4 Interpretation and Use of Proton and Carbon Coupling Constants

Ch. 5 Multiple-Pulse and Multidimensional NMR Techniques

Ch. 6 Mass Spectrometry: Core Techniques and Ionization Processes

Ch. 7 Mass Spectrometry Analysis of Small and Large Molecules

Ch. 8 Fragmentation Processes in Electron Ionization Mass Spectrometry

Ch. 9 Infrared Spectroscopy

Ch. 10 Optical and Chiroptical Techniques: Ultraviolet Spectroscopy

Ch. 11 Strategies of Determining Structure and Stereochemistry: Spectroscopic Data Translated Into Structures

Ch. 12 Problems in Organicstructure Analysis

Appendix A Collection of Spectra or Data Tables

Appendix B Shape of MS Clusters

Appendix C CAS Registry Numbers for Unknowns

Appendix D Glossary and Abbreviations

Index