Organic chemistry

The Organic Chem Lab
Survival Manual
A Student's Guide
to Techniques

James W. Zubrick
Hudson Valley Community College

John Wiley & Sons
N ew York

Chichester

Brisbane

Toronto

Singapore

Copyright O 1984,1988, y John Wiley & Sons, Inc.
b
All rights resewed. Published simultaneously in Canada.
Reproduction or translation of any part of
this work beyond that permitted bySections
107 a nd 108 of the 1976 United States Copyright
Act without the permission of the copyright
owner is unlawful. Requests for permission
or further information should be addressed to
the Permissions Department, John Wiley & Sons.

Library of Congress Cataloging-in-Publication Data
Zubrick, James W.
The organic chem lab survival manual.
Includes indexes.
1 Chemistry,Organic-Laboratory manuals.
.
I. Title.
QD261.Z83 1988
57.08
4'07
87-20968
ISBN 0-471-85519-7
(pbk.)
Printed in the United States of America

T o C indy

Preface to the
d
Second E ition
I t is heartening to hear of your book being read and enjoyed, literally cover to
cover, by individuals ranging from talented high-school science students to
Professors Emeritus of the English language.Even better to hear that you
have a chance to improve that book, based upon the above comments,
comments by reviewers, and the experience gained from working with the
text.
In this edition of The Organic Chem Lab Survival Manual, t he section on
notebooks and handbooks have been expanded to include typical notebook
pages and actual handbook entries along with interpretation. There are newnotes on cleaning and drying glassware, and how to find a good recrystallization solvent. Once their samples are purified, students may now find directions for taking a melting point with the Thomas-Hoover apparatus. Washing has been given the same importance as extraction, and a few more trouble
spots -taking the pH of an organic layer, for one -have been smoothed.
There are additionalinstructions on steam distillation using external sources
of steam. Simple manometers, coping with air leaks, and the correct use of a
pressure- temperature nomograph enhance the section on vacuum distillation. Refractometry has been added, as well as-by special requestsections on the theory of extraction and distillation, including azeotropes and
azeotropic distillation, and, I believe, the firstapplication of the ClausiusClapyron equation as a bridge for getting from Raoult's Law (pressure and
mole fraction) to the phase diagram (temperature and mole fraction).
Many people deserve credit for their assistance in producing this edition:
my students, for helping me uncover what was lacking in the previous edition,
with Mr. Ronald Pohadsky and Mr. Barry Eggleston making specific suggestionswhile working in the laboratory. A special thanks to Professor G.J. Janz,
director of the Molten Salts Data Center at the Rensselaer Polytechnic Institute for his review of the physical chemistry sections of this edition, and to
Professors Henry Hollinger and A. Rauf Imam for their help during the initial
phases of that work. I would also like to thank
William Epstein
University of Utah
RudolphGoetz
Michigan State University

PREFACE TO T E SECOND EDITION
H

Clelia W. Mallory
University of Pennsylvania
J. Wolinsky
Purdue University
for their valuable comments and suggestions in making this edition more
useful for students of organic chemistry laboratory.
Finally, I'd like to thank Mr. Dennis Sawicki, Chemistry Editor at John
Wiley & Sons, first, for one of the nicestbirthday presents I've gotten in a
while, and second, for his encouragement, guidance, and patience at some
troubling points in the preparation of this edition. Ms. Dawn Reitz, Production Supervisor, Ms. Ann Meader, Supervising Copy Editor, and Mr. Glenn
Petry, Copy Editor deserve a great deal of credit in bringing this second
edition about.
J. W. Zubrick
Hudson Valley Community College
April...