Organic Spectroscopy Workbook

Spectroscopy is used in physical and analytical chemistry for the identification of substances through the spectrum emitted from or absorbed by them. The derivation of structural information from spectroscopic data is now an integral part of many courses in chemistry and related subjects at most universities. This workbook: Features exercises to help develop the student′s understanding of how structures are determined from spectra and to promote the student′s own interpretation of different spectra. Covers a large range of spectroscopic data, including mass spectrometry, infrared and 1 H and 13 C nuclear magnetic resonance, typically used in the routine analysis of small–sized organic molecules. Presents in full–color, in a workbook–friendly format the spectra for interpretation with explanations and analyses on the facing page. Related to the workbook the authors have an online resource of the problems featured in the workbook, available at: htttp://spectros.unice.fr/ By using the print edition alongside the online spectra, students will be able to enhance their understanding of the interpretation of multiple spectra. Appropriate for undergraduate and postgraduate students alike, Organic Spectroscopy Workbook eases the beginner into the process, acting as a valuable teaching tool and an essential bench top reference guide for determining structures using spectral data. This book offers complete and valuable explanations at the student′s fingertips.

Preface vii Acknowledgements ix How to Use this Workbook 1 Preliminary Observations 2 Centres of Unsaturation 8 Exercises 1–100 10 Infrared Data 210 IR Frequencies: Display of Infrared Database by Frequency 210 IR Groups: Display of Infrared Database by Functional Group 216 1 H NMR Data 221 General Tables of Functional Groups 221 Comparison of δ of Alkyl Groups Bearing a Substituent in α or β Position 225 Alkyl Groups with an α Substituent 226 Alkyl Groups with a β Substituent 226 Tables of δ for −CH2− Doubly Substituted in α Position 227 Tables of δ for Aromatics 229 Coupling Constants 230 13 C NMR Data 233 General Ranges for CH3−, −CH2−, > CH− . . . 233 Chemical Shift Ranges for Functional Groups 234 Chemical Shift Estimations 234 Mass Spectrometry Data 240 Main Fragments Observed 240 Atomic Masses 242 Isotopic Abundances in % 243 Internet Resources 254 Glossary of Terms Used in the Exercises 255 Answers 257 Index 261

Tom Forrest Department of Chemistry, Dalhousie University, Canada Jean–Pierre Rabine Centre de Développement Informatique Enseignement Chimie, Université de Nice Sophia–Antipolis, France Michel Rouillard Centre de Développement Informatique Enseignement Chimie, Université de Nice Sophia–Antipolis, France