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The Organic Chem Lab Survival Manual
A Student's Guide to Techniques James W. Zubrick
Hudson Valley Community College

John Wiley & Sons
New York • Chichester • Brisbane • Toronto • Singapore

Copyright © 1984,1988, by John Wiley & Sons, Inc. All rights reserved. Published simultaneously in Canada. Reproduction or translation of any part of this work beyond that permitted by Sections 107and 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 547'.0078 87-20968 ISBN 0-471-85519-7 (pbk.) Printed in the United States of America 10 9 8 7 6

To Cindy

Preface to the Second Edition
It 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 youhave 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 OrganicChem Lab Survival Manual, the section on notebooks and handbooks have been expanded to include typical notebook pages and actual handbook entries along with interpretation. There are new notes 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 additional instructions on steam distillation usingexternal 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 request— sections on the theory of extraction and distillation, including azeotropes and azeotropic distillation, and, I believe, the first application of the ClausiusClapyron equationas 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 suggestions while working in the laboratory. A specialthanks 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 Rudolph Goetz Michigan State University

viiiClelia W. Mallory University of Pennsylvania J. Wolinsky Purdue University

PREFACE TO THE SECOND EDITION

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 nicest birthday 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 3, 1987

Preface to the First Edition
Describe, for...