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Full Description
The derivation of structural information from spectroscopic data is now an integral part of organic chemistry courses at all Universities. A critical part of any such course is a suitable set of problems to develop the students' understanding of how organic structures are determined from spectra. The book builds on the very successful teaching philosophy of learning by hands-on problem solving; carefully graded examples build confidence and develop and consolidate a student's understanding of organic spectroscopy.Organic Structures from Spectra, 6th Edition is a carefully chosen set of about 250 structural problems employing the major modern spectroscopic techniques, including Mass Spectrometry, 1D and 2D 13C and 1H NMR Spectroscopy and Infrared Spectroscopy. There are 25 problems specifically dealing with the interpretation of spin-spin coupling in proton NMR spectra and 10 problems based on the quantitative analysis of mixtures using proton and carbon NMR spectroscopy. The accompanying text is descriptive and only explains the underlying theory at a level that is sufficient to tackle the problems. The text includes condensed tables of characteristic spectral properties covering the frequently encountered functional groups.The examples themselves have been selected to include all important structural features and to emphasise connectivity arguments and stereochemistry. Many of the compounds were synthesised specifically for this book. In this collection, there are many additional easy problems designed to build confidence and to demonstrate basic principles.The Sixth Edition of this popular textbook:now incorporates many new problems using 2D NMR spectra (C-H Correlation spectroscopy, HMBC, COSY, NOESY and TOCSY);has been expanded and updated to reflect the new developments in NMR spectroscopy;has an additional 40 carefully selected basic problems;provides a set of problems dealing specifically with the quantitative analysis of mixtures using NMR spectroscopy;features proton NMR spectra obtained at 200, 400 and 600 MHz and 13C NMR spectra including routine 2D C-H correlation, HMBC spectra and DEPT spectra;contains a selection of problems in the style of the experimental section of a research paper;includes examples of fully worked solutions in the appendix;has a complete set of solutions available to instructors and teachers from the authors.Organic Structures from Spectra, Sixth Edition will prove invaluable for students of Chemistry, Pharmacy and Biochemistry taking a first course in Organic Chemistry.
Contents
Preface ixList of Tables xiiiList of Figures xv1 Introduction 11.1 General Principles of Absorption Spectroscopy 11.2 Chromophores 21.3 Degree of Unsaturation 31.4 Connectivity 41.5 Sensitivity 41.6 Practical Considerations 52 Ultraviolet (UV) Spectroscopy 62.1 The Nature of Ultraviolet Spectroscopy 62.2 Basic Instrumentation 62.3 Quantitative Aspects of Ultraviolet Spectroscopy 82.4 Classification of UV Absorption Bands 82.5 Special Terms in Ultraviolet Spectroscopy 92.6 Important UV Chromophores 102.6.1 Dienes and Polyenes 102.6.2 Carbonyl Compounds 112.6.3 Benzene Derivatives 112.7 The Effect of Solvents 133 Infrared (IR) Spectroscopy 143.1 Absorption Range and the Nature of IR Absorption 143.2 Experimental Aspects of Infrared Spectroscopy 153.3 General Features of Infrared Spectra 163.4 Important IR Chromophores 183.4.1 -O-H and -N-H Stretching Vibrations 183.4.2 C-H Stretching Vibrations 183.4.3 -C N and -C C- Stretching Vibrations 193.4.4 Carbonyl Groups 193.4.5 Other Polar Functional Groups 213.4.6 The Fingerprint Region 214 Mass Spectrometry 234.1 Ionisation Processes 234.2 Instrumentation 254.3 Mass Spectral Data 264.3.1 High Resolution Mass Spectra 264.3.2 Molecular Fragmentation 284.3.3 Isotope Ratios 294.3.4 Chromatography Coupled With Mass Spectrometry 314.3.5 Metastable Peaks 314.4 Representation of Fragmentation Processes 314.5 Factors Governing Fragmentation Processes 324.6 Examples of Common Types of Fragmentation 324.6.1 Cleavage at Branch Points 324.6.2 -Cleavage 334.6.3 Cleavage to Carbonyl Groups 334.6.4 Cleavage to Heteroatoms 344.6.5 Retro Diels-Alder Reaction 344.6.6 The Mclafferty Rearrangement 345 1H Nuclear Magnetic Resonance (NMR) Spectroscopy 365.1 The Physics of Nuclear Spins and NMR Instruments 365.1.1 The Larmor Equation and Nuclear Magnetic Resonance 365.2 Basic NMR Instrumentation 395.2.1 CW and Pulsed NMR Spectrometers 395.2.2 Nuclear Relaxation 425.2.3 Magnets for NMR Spectroscopy 435.2.4 The NMR Spectrum 445.3 Chemical Shift in 1H NMR Spectroscopy 455.4 Spin-Spin Coupling in 1H NMR Spectroscopy 525.4.1 Signal Multiplicity - The N+1 Rule 545.5 Analysis of 1H NMR Spectra 555.5.1 Spin Systems 565.5.2 Strongly and Weakly Coupled Spin Systems 565.5.3 Magnetic Equivalence 585.5.4 Conventions for Naming Spin Systems 595.5.5 Spectral Analysis of First-Order NMR Spectra 605.5.6 Splitting Diagrams 615.5.7 Spin Decoupling 645.6 Correlation of 1H-1H Coupling With Structure 655.6.1 Non-Aromatic Spin Systems 655.6.2 Aromatic Spin Systems 665.7 The Nuclear Overhauser Effect (NOE) 695.8 Labile and Exchangeable Protons 706 13c NMR Spectroscopy 726.1 Coupling and Decoupling in 13c NMR Spectra 726.2 The Nuclear Overhauser Effect (NOE) in 13c NMR Spectroscopy 736.3 Determining 13c Signal Multiplicity Using Dept 736.4 Shielding and Characteristic Chemical Shifts in 13c NMR Spectra 767 2-Dimensional NMR Spectroscopy 827.1 Proton-Proton Interactions By 2D NMR 857.1.1 COSY (Correlation Spectroscopy) 857.1.2 TOCSY (Total Correlation Spectroscopy) 867.1.3 NOESY (Nuclear Overhauser Effect Spectroscopy) 887.2 Proton-Carbon Interactions By 2D NMR 897.2.1 The HSQC (Heteronuclear Single Quantum Correlation) or HSC (Heteronuclear Shift Correlation) Spectrum 897.2.2 HMBC (Heteronuclear Multiple Bond Correlation) 918 Miscellaneous Topics 968.1 Solvents for NMR Spectroscopy 968.2 Solvent-Induced Shifts 978.3 Dynamic Processes in NMR - The NMR Time-Scale 988.3.1 Conformational Exchange Processes 998.3.2 Intermolecular Exchange of Labile Protons 998.3.3 Rotation About Partial Double Bonds 1008.4 The Effect of Chirality 1008.5 The NMR Spectra of "Other Nuclei" 1019 Determining the Structure of Organic Compounds From Spectra 1029.1 Solving Problems 1039.2 Worked Examples 10410 Problems 115Index 538
