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Organic Experiments
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Experiments
Seventh Edition
Louis F. Fieser
Late Professor Emeritus
Harvard University
Kenneth L Williamson
Mount Holyoke College
D. C. HEATH AND COMPANY
Lexington, Massachusetts
Toronto
Address editorial correspondence to:
D. C. Heath
125 Spring Street
Lexington, MA 02173
Cover: Charlotte Raymond/Science Source/Photo Researchers, Inc.
Copyright © 1992 by D. C. Heath and Company.
Previous editions copyright © 1987, 1983, 1979, 1975, 1968, and 1964 by D. C.
Heath and Company.
All rights reserved. No part of this publication may be reproduced or
transmitted in any form or by any means, electronic or mechanical, including
photocopy, recording, or any information storage or retrieval system, without
permission in writing from the publisher.
Published simultaneously in Canada.
Printed in the United States of America.
International Standard Book Number: 0-669-24344-2
Library of Congress Catalog Number: 91-71287
10 9 8 7 6 5 4
Preface
Organic Experiments,
Seventh Edition, presents to the beginning student a
series of clear and concise experiments that encourage accurate observa-
tion and the development of deductive reasoning.
New to this edition is the section at the end of every experiment
entitled "Cleaning Up," which has been written with the intent of focusing
students' attention not just on the desired product from a reaction, but also
on all of the other substances produced in a typical organic reaction.
Throughout the text most, but not all, of the 60 and 90 MHz nmr spectra
have been replaced with 250 MHz proton spectra. A section on 2D nmr is
included in the chapter on nmr spectroscopy, and procedures are given for
the use of chiral nmr shift reagents to determine the optical purity of the
product from the chiral enzymatic reduction of a ketone.
A number of small changes have been made so that
Organic Experi-
ments
reflects the very latest and best of organic chemistry. Nomenclature
revision is a continuous process. Gradually names such as isoamyl alcohol
are being replaced by their IUPAC equivalents, but slavish adherence to
those rules is not followed; phenol is still phenol (and not benzenol).
As a coauthor of
Prudent Practices for the Disposal of Chemicals from
Laboratories,
National Academy of Sciences, Washington, D.C., 1983, I
have continued to follow closely the rapidly evolving regulatory climate and
changes in laboratory safety rules and regulations. The safety information in
this text is as current as it can be, but this is a rapidly changing area of
chemistry; local rules and regulations must be known and adhered to.
Range of Experiments
Organic Experiments
includes a wide range of experiments and experimen-
tal procedures:
Pelletized Norit is introduced (Chapter 3). It is easily handled and the
progress of decolorization is easily followed.
Several polymers can be synthesized (Chapter 67), enzymes are used
to carry out chiral reduction of a ketone (Chapter 64), and a unique
synthesis of ferrocene is presented (Chapter 29).
Many of the experiments are classics introduced by Louis Fieser, for
example, the isolation of cholesterol from human gallstones, the use of very
high boiling solvents to speed syntheses of such compounds as
tetraphenylcyclopentadiene and /?-terphenyl, and the Martius Yellow ex-
periment (Chapter 61).

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