Organic Structures from Spectra E-Book

L. D. Field

• Herausgeber: John Wiley & Sons
• Kategorie: Wissenschaft und neue Technologien
• Sprache: Englisch

Seitenzahl: 213

Veröffentlichungsjahr: 2020

Beschreibung

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.

Leseprobe

Table of Contents

COVER

PREFACE

LIST OF TABLES

LIST OF FIGURES

1 INTRODUCTION

1.1 GENERAL PRINCIPLES OF ABSORPTION SPECTROSCOPY

1.2 CHROMOPHORES

1.3 DEGREE OF UNSATURATION

1.4 CONNECTIVITY

1.5 SENSITIVITY

1.6 PRACTICAL CONSIDERATIONS

2 ULTRAVIOLET (UV) SPECTROSCOPY

2.1 THE NATURE OF ULTRAVIOLET SPECTROSCOPY

2.2 BASIC INSTRUMENTATION

2.3 QUANTITATIVE ASPECTS OF ULTRAVIOLET SPECTROSCOPY

2.4 CLASSIFICATION OF UV ABSORPTION BANDS

2.5 SPECIAL TERMS IN UV SPECTROSCOPY

2.6 IMPORTANT UV CHROMOPHORES

2.7 THE EFFECT OF SOLVENTS

3 INFRARED (IR) SPECTROSCOPY

3.1 ABSORPTION RANGE AND THE NATURE OF IR ABSORPTION

3.4 IMPORTANT IR CHROMOPHORES

4 MASS SPECTROMETRY

4.1 IONISATION PROCESSES

4.2 INSTRUMENTATION

4.3 MASS SPECTRAL DATA

4.4 REPRESENTATION OF FRAGMENTATION PROCESSES

4.5 FACTORS GOVERNING FRAGMENTATION PROCESSES

4.6 EXAMPLES OF COMMON TYPES OF FRAGMENTATION

5

1

H NUCLEAR MAGNETIC RESONANCE (NMR) SPECTROSCOPY

5.1 THE PHYSICS OF NUCLEAR SPINS AND NMR INSTRUMENTS

5.2 BASIC NMR INSTRUMENTATION AND THE NMR EXPERIMENT

5.3 CHEMICAL SHIFTS IN 1H NMR SPECTROSCOPY

5.4 SPIN–SPIN COUPLING IN 1H NMR SPECTROSCOPY

5.5 ANALYSIS OF 1H NMR SPECTRA

5.6 CORRELATION OF 1H–1H COUPLING WITH STRUCTURE

5.7 THE NUCLEAR OVERHAUSER EFFECT (NOE) IN 1H NMR SPECTROSCOPY

5.8 LABILE AND EXCHANGEABLE PROTONS

REFERENCES

6

13

C NMR SPECTROSCOPY

6.1 COUPLING AND DECOUPLING IN

13

C NMR SPECTRA

6.2 THE NUCLEAR OVERHAUSER EFFECT (NOE) IN 13C NMR SPECTROSCOPY

6.3 DETERMINING 13C SIGNAL MULTIPLICITY USING DEPT

6.4 SHIELDING AND CHARACTERISTIC CHEMICAL SHIFTS IN 13C NMR SPECTRA

7 2-DIMENSIONAL NMR SPECTROSCOPY

7.1 PROTON–PROTON INTERACTIONS BY 2D NMR

7.2 PROTON–CARBON INTERACTIONS BY 2D NMR

8 MISCELLANEOUS TOPICS

8.1 SOLVENTS FOR NMR SPECTROSCOPY

8.2 SOLVENT-INDUCED SHIFTS

8.3 DYNAMIC NMR SPECTROSCOPY – THE NMR TIME-SCALE

8.4 THE EFFECT OF CHIRALITY

8.5 THE NMR SPECTRA OF “OTHER NUCLEI”

9 DETERMINING THE STRUCTURE OF ORGANIC COMPOUNDS FROM SPECTRA

Collection of Spectra

9.1 SOLVING PROBLEMS

9.2 WORKED EXAMPLES

10 PROBLEMS

Problem 1

Problem 2

Problem 3

Problem 4

Problem 5

Problem 6

Problem 7

Problem 8

Problem 9

Problem 10

Problem 11

Problem 12

Problem 13

Problem 14

Problem 15

Problem 16

Problem 17

Problem 18

Problem 19

Problem 20

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Problem 22

Problem 23

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INDEX

END USER LICENSE AGREEMENT

List of Tables

Chapter 2

Table 2.1 Observable UV Absorption Bands for Acetophenone

Table 2.2 The Effect of Extended Conjugation on UV Absorption

Table 2.3 UV Absorption Bands in Common Carbonyl Compounds

Table 2.4 UV Absorption Bands in Common Benzene Derivatives

Chapter 3

Table 3.2 C–H IR Absorption Frequencies in Common Functional Groups

Table 3.3 C≡N and C≡C Absorption Frequencies in Common Functional Groups...

Table 3.4 C=O IR Absorption Frequencies in Common Functional Groups

Table 3.5 Characteristic IR Absorption Frequencies for Functional Groups

Chapter 4

Table 4.1 Accurate Masses of Selected Isotopes

Table 4.2 Common Fragments and their Masses

Chapter 5

Table 5.1 Nuclear Spins and Magnetogyric Ratios for Common NMR-Active Nuclei...

Table 5.2 Resonance Frequencies of 1H and 13C Nuclei in Magnetic Fields of Dif...

Table 5.3 Typical 1H Chemical Shift Values (δ) in Selected Organic Comp...

Table 5.4 Typical

1

H Chemical Shift Values (δ) of Selected P...

Table 5.5 1H Chemical Shift Values (δ) for Protons in Common Alkyl Deri...

Table 5.7 Approximate

1

H Chemical Shifts (δ) for Olefinic Protons

Table 5.8 Approximate 1H Chemical Shifts (δ) for Aromatic Protons in Be...

Table 5.9 1H Chemical Shifts (δ) for Protons in some Polynuclear Aromat...

Table 5.10 Typical

1

H–

1

H Coupling Constants

Table 5.11 Relative Line Intensities for Simple Multiplets

Table 5.12 Proton–Proton Coupling Constants in Aromatic and Heteroaromatic Rin...

Chapter 6

Table 6.1 The Number of Aromatic 13C Resonances in Benzenes with Different Sub...

Table 6.2 Typical 13C Chemical Shift Values in Selected Organic Compounds...

Table 6.3 Typical

13

C Chemical Shift Ranges in Organic Compounds

Table 6.5 13C Chemical Shifts (δ) for sp3-hybridised Carbons in Alkyl D...

Table 6.6 13C Chemical Shifts (δ) for sp2-hybridised Carbons in Vinyl D...

Table 6.7 13C Chemical Shifts (δ) for sp-hybridised Carbons in Alkynes ...

Table 6.8 Approximate 13C Chemical Shifts (δ) for Aromatic Carbons in ...

Table 6.9 Characteristic 13C Chemical Shifts (δ) in some Polynuclear A ...

Chapter 8

Table 8.1 1H and 13C Chemical Shifts for Common NMR solvents

List of Illustrations

Chapter 1

Figure 1.1 Schematic Absorption Spectrum

Figure 1.2 Definition of a Spectroscopic Transition

Chapter 2

Figure 2.1 Schematic Representation of an IR or UV Spectrometer

Figure 2.2 Schematic Representation of a Double-Beam Absorption Spectrometer...

Figure 2.3 Definition of Absorbance (A)

Chapter 4

Figure 4.1 Schematic Mass Spectrum

Figure 4.2 Schematic Diagram of an Electron-Impact Magnetic Sector Mass Spect...

Figure 4.3 Relative Intensities of the Cluster of Molecular Ions for Molecule...

Chapter 5

Figure 5.1 A Spinning Positive Charge Generates a Magnetic Field and Behaves l...

Figure 5.2 Schematic Representation of a CW NMR Spectrometer

Figure 5.3 Schematic Representation of a Pulsed NMR Spectrometer

Figure 5.4 1H NMR Spectra: (a) Time Domain Spectrum (FID); (b) Frequency Domai...

Figure 5.5

1

H NMR Spectrum of Bromoethane (400 MHz, CDCl

3

)

Figure 5.6 Shielding/deshielding Zones for Common Non-aromatic Functional Grou...

Figure 5.7 1H NMR Spectrum of Bromoethane (400 MHz, CDCl3) Showing the Multip...

Figure 5.8 Characteristic Multiplet Patterns for Common Organic Fragments...

Figure 5.9 Aromatic Region of the 1H NMR Spectrum of 2-Bromotoluene (acetone-...

Figure 5.10 Simulated 1H NMR Spectra of a 2-Spin System as the Ratio ...

Figure 5.11 A Portion of the 1H NMR Spectrum of Styrene Epoxide (100 ...

Figure 5.12 The 60 MHz

1

H NMR Spectrum of a 4-Spin AMX...

Figure 5.13 Selective Decoupling in the

1

H NMR Spectrum of Bromoethane...

Figure 5.14 Selective Decoupling in a Simple 4-Spin System

Figure 5.15 Characteristic Aromatic Splitting Patterns in the 1H NMR Spectra ...

Figure 5.16 Characteristic Aromatic Splitting Patterns in the 1H NMR Spectra ...

Figure 5.17 1H NMR Spectrum of p-Nitrophenylacetylene (200 MHz as a 10% solut...

Figure 5.18 Aromatic Region of the 1H NMR Spectrum of 2,4-Dinitrotoluene. (i)...

Figure 5.19 D2O Exchange in the 1H NMR Spectrum of 1-Propanol (300 MHz, CDCl3...

Chapter 6

Figure 6.1 13C NMR Spectra of Methyl Cyclopropyl Ketone (CDCl3 solvent, 100 M...

Chapter 7

Figure 7.1 Acquisition of a 2D NMR spectrum: a series of individual FIDs are ...

Figure 7.2 Representations of 2D NMR Spectra: (a) Stacked Plot; (b) Contour P...

Figure 7.3 Representations of Phase-sensitive 2D NMR Spectra: (a) Stacked Plo...

Figure 7.4

1

H COSY Spectrum of 1-Iodobutane (CDCl

3

solvent, 298K, 400 MHz)

Figure 7.5 1H TOCSY Spectrum of Butyl Ethyl Ether (CDCl3 solvent, 298K, 400 MH...

Figure 7.6 1H NOESY Spectrum of β-Butyrolactone (CDCl3 solvent, 298K, 600 MHz)...

Figure 7.7 1H–13C me-HSQC Spectrum of 1-Iodobutane (CDCl>3 solvent, 298K, 1H 4...

Figure 7.8 1H–13C HMBC Spectrum of 1-Iodobutane (CDCl3 solvent, 298K, 1H 400 ...

Figure 7.9 1H–13C HMBC Spectrum of 2-Bromophenol (CDCl3 solvent, 298K, 1H 400...

Chapter 8

Figure 8.1 Schematic NMR Spectra of Two Exchanging Nuclei

Figure 8.2

1

H NMR Spectrum of the Aliphatic Region of Cysteine

Guide

Cover

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Organic Structures from Spectra

Sixth Edition

L. D. Field

Professor of Chemistry

School of Chemistry

University of New South Wales, Australia

H. L. Li

Senior Research Associate

School of Chemistry

University of New South Wales, Australia

A. M. Magill

Honorary Research Associate

School of Chemistry

University of New South Wales, Australia

This edition first published 2020

© 2020 John Wiley & Sons Ltd

Edition History

John Wiley & Sons (4e, 2008)

John Wiley & Sons (5e, 2013)

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Library of Congress Cataloging-in-Publication Data

Names: Field, L. D., author.

Title: Organic structures from spectra / L.D. Field, Professor of

Chemistry, School of Chemistry, University of New South Wales, H.L.

Li, Senior Research Fellow, School of Chemistry, University of New South

Wales, A.M. Magill, Honorary Research Fellow, School of Chemistry, University of New South Wales.

Description: Sixth edition. | Hoboken, NJ : Wiley, 2020. | Includes bibliographical references and index.

Identifiers: LCCN 2020004972 (print) | LCCN 2020004973 (ebook) | ISBN 9781119524809 (paperback) | ISBN 9781119524793 (adobe pdf) | ISBN 9781119524847 (epub)

Subjects: LCSH: Spectrum analysis–Problems, exercises, etc. | Organic compounds–Structure–Problems, exercises, etc.

Classification: LCC QD272.S6 S74 2020 (print) | LCC QD272.S6 (ebook) | DDC 543/.17—dc23

LC record available at https://lccn.loc.gov/2020004972

LC ebook record available at https://lccn.loc.gov/2020004973

Cover Design: Wiley

Cover Image: Courtesy of Professor L. D. Field, Dr. Hsiu Lin Li and Dr. Alison Magill; © Chernookaya/Shutterstock

PREFACE

This is the Sixth Edition of the text “Organic Structures from Spectra”. The original text, published in 1986 by J R Kalman and S Sternhell, was a remarkable instructive text at a time where spectroscopic analysis, particularly NMR spectroscopy, was becoming widespread and routinely available in many chemical laboratories. The original text was founded on the premise that the best way to learn to obtain “structures from spectra” is to build up skills by practising on simple problems. Editions two through five of the text have been published at about five-yearly intervals and each revision has taken account of new developments in spectroscopy as well as dropping out techniques that have become less important or obsolete over time. The collection has grown substantially and we are deeply indebted to Dr John Kalman and to Emeritus Professor Sev Sternhell for their commitment and contribution to all of the previous editions of “Organic Structures from Spectra”.

Edition Six of the text has been expanded to include a new selection of problems and many of the problems now incorporate 2D NMR spectra (COSY, TOCSY, NOESY, C–H Correlation spectroscopy or HMBC).

The overarching philosophy remains the same as in previous editions of the text:

Theoretical exposition is kept to a minimum, consistent with gaining an understanding of those aspects of the various spectroscopic techniques which are actually used in solving problems. Experience tells us that both mathematical detail and in-depth theoretical description of advanced techniques merely confuse or overwhelm the average student.