Vogel's Textbook Of Practical Organic Chemistry

VOGEL's TEXTBOOK OF PRACTICAL ORGANIC CHEMISTRY FIFTH EDITION Revised by former and current members of The School of Chemistry, Thames Polytechnic, London Brian S. Furniss Antony J. Hannaford Peter W. G. Smith Austin R. Tatchell ~ .. ~ ...... ...... ~ Longman Scientific & ~rechni nice1 Copublished in the United States with John Wiley & Sons, Inc., New York Longman Scientific & Technical Longman Group UK Limited Longman House, Burnt Mill, Harlow Essex CM20 2JE, England and Associated Companies throughout the world Copublished in the United States with John Wiley & Sons, lnc., 605 Third Avenue, New York, NY 10158 © Longman Group UK Limited 1989 All rights reserved; no part of this publication may be reproduced, stored in a retrieval system, or transmitted in any form or by any means, electronic, mechanical, photocopying, recording, or otherwise, without either the prior written permission of the Publishers, or a licence permitting restricted copying in the United Kingdom issued by the Copyright Licensing Agency Ltd, 33-34 Alfred Place, London, WCIE 7DP. First published 1948 New Impression with minor corrections, October 1948 Second Edition 1951 New Impression with addition of Chapter XII on Semimicro Technique 1954 Third Edition 1956 New Impression with corrections and additions 1957 New Impressions 1959, 1961, 1962, 1964, 1965, 1967 Fourth Edition 1978 Reprinted, with minor corrections 1979, 1981, 1984, 1986, 1987, 1988 Fifth Edition 1989 British Library Cataloguing in Publication Data Vogel, Arthur Israel Vogel's textbook of practical organic chemistry 5th ed I. Organic chemistry. Laboratory techniques I. Title I. Furniss, B. S. (Brian Stanley), 1941 547..'0028 ISBN 0-582-46236-3 Library of Congress Cataloging-in-Publication Data Vogel, Arthur Israel. Vogel's Textbook of practical organic chemistry - 5th ed. / rev. by Brian S. Furniss ... [et al.] p. cm. Fourth ed. published in 1978 under title: Vogel's Textbook of practical organic chemistry, including qualitative organic analysis. Includes bibliographies and indexes. ISBN 0-470-21414-7 1. Chemistry, Organic-Laboratory manuals. 2. Chemistry, Analytic-Qualitative. I. Furniss, Brian S. (Brian Stanley), 194111. Vogel, Arthur Israel. Vogel's Textbook of practical organic chemistry, including qualitative organic analysis. Ill. Title. QD26I.V63 1989 547-dc19 88-36786 CIP Set in 10/11 pt. Lasercomp Times New Roman Filmset by Eta Services (Typesetters) Ltd, Beccles, Suffolk Printed in Great Britain by The Bath Press CONTENTS CHAPTER 1 ORGANIC SYNTHESIS 1.1 INTRODUCTION 1.2 STRUCTURE OF THE TARGET MOLECULE 1.3 REACTION MECHANISM AND THE METHODOLOGY OF SYNTHESIS 1.4 REACTION MECHANISM AND THE STRATEGY OF SYNTHESIS 1.5 CONCLUSION 1 2 10 17 23 REFERENCES 23 CHAPTER 2 EXPERIMENTAL TECHNIOUES 26 2.1 GENERAL INSTRUCTIONS FOR SAFE WORKING IN ORGANIC CHEMICAL LABORATORIES 2.2 PLANNING OF EXPERIMENTS AND RECORDING OF RESULTS 2.3 HAZARDS IN ORGANIC CHEMISTRY LABORATORIES 2.3.1 Introduction 34 2.3.2 Explosion and fire hazards 35 2.3.3 Reactive inorganic reagents 42 2.3.4 Hazards due to toxic chemicals 44 2.3.5 Electrical safety 51 2.3.6 Ultraviolet radiation 52 APPARATUS AND REACTION PROCEDURES 2.4 INTERCHANGEABLE GROUND GLASS JOINTS 2.5 TYPES OF GROUND GLASS JOINTS 2.6 CARE AND MAINTENANCE OF GROUND GLASS JOINTS 2.7 APPARATUS WITH INTERCHANGEABLE GROUND GLASS JOINTS SUITABLE FOR GENERAL USE IN PREPARATIVE ORGANIC CHEMISTRY 2.8 OTHER TYPES OF INTERCHANGEABLE JOINTS AND STOPCOCKS 2.9 THE USE OF CORKS AND RUBBER STOPPERS 2.10 CUTTING AND BENDING OF GLAS