Table Of ContentNINTH EDITION
THE ORGANIC
CHEM LAB
SURVIVAL MANUAL
A Student’s Guide to Techniques
JAMES W. ZUBRICK
Hudson Valley Community College
For Zoë and Anne,
who make it all worth the effort.
VP & Executive Publisher Kaye Pace
Associate Publisher Petra Recter
Sponsoring Editor Joan Kalkut
Editorial Assistant Ashley Gayle
Marketing Manager Kristine Ruff
Marketing Assistant Andrew Ginsberg
Designer Seng Ping Ngieng
Associate Production Manager Joyce Poh
Production Editor Jolene Ling
This book was set in 10/12 Times by Aptara®, Inc. and printed and bound by
Courier Westford. The cover was printed by Courier Westford.
This book is printed on acid free paper.
Founded in 1807, John Wiley & Sons, Inc. has been a valued source of knowledge and understanding
for more than 200 years, helping people around the world meet their needs and fulfi ll their aspirations.
Our company is built on a foundation of principles that include responsibility to the communities we
serve and where we live and work. In 2008, we launched a Corporate Citizenship Initiative, a global
effort to address the environmental, social, economic, and ethical challenges we face in our business.
Among the issues we are addressing are carbon impact, paper specifi cations and procurement, ethical
conduct within our business and among our vendors, and community and charitable support. For more
information, please visit our website: www.wiley.com/go/citizenship.
Copyright © 2014, 2011, 2008, 2004 John Wiley & Sons, Inc. 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, scanning or otherwise, except as permitted under
Sections 107 or 108 of the 1976 United States Copyright Act, without either the prior written
permission of the Publisher, or authorization through payment of the appropriate per-copy fee
to the Copyright Clearance Center, Inc. 222 Rosewood Drive, Danvers, MA 01923, website
www.copyright.com. Requests to the Publisher for permission should be addressed to the Permissions
Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030-5774, (201)748-6011,
fax (201)748-6008, website http://www.wiley.com/go/permissions.
Evaluation copies are provided to qualifi ed academics and professionals for review purposes only, for use in
their courses during the next academic year. These copies are licensed and may not be sold or transferred
to a third party. Upon completion of the review period, please return the evaluation copy to Wiley. Return
instructions and a free of charge return mailing label are available at www.wiley.com/go/returnlabel. If you
have chosen to adopt this textbook for use in your course, please accept this book as your complimentary
desk copy. Outside of the United States, please contact your local sales representative.
Library of Congress Cataloging-in-Publication Data
Zubrick, James W.
The organic chem lab survival manual a student’s guide to techniques/James W. Zubrick, Hudson Valley
Community College.—Ninth ed.
p. cm.
Includes index.
ISBN 978-1-118-08339-0 (pbk. : alk. paper)
1. Chemistry, Organic—Laboratory manuals. I. Title.
QD261.Z83 2012
547.0078—dc23
2012020179
Printed in the United States of America
10 9 8 7 6 5 4 3 2 1
PREFACE TO THE
NINTH EDITION
This Survival Manual again presents the basic techniques of the organic chemistry
laboratory, with the usual emphasis on doing the work correctly the fi rst time. And
once again, I have relied on the comments of users and reviewers in guiding the
changes and additions that have been made.
Safety in the laboratory, always a primary concern, now has to consider the
addition of such technology as the iPad, the Nook, the Kindle, and even text mes-
saging, where applicable. Microscale, also where applicable, has been reviewed and
u pdated as well. And while currently resisting the deletion of double-beam spectro-
photometers altogether, a discussion of the technique of Attenuated Total Refl ectance
and associated practices has been added to the section on Infrared Spectroscopy
(Chapter 32).
The discussion and presentation of the section on Nuclear Magnetic Reso-
nance (Chapter 33) has been re-worked such that the different methods of sample
preparation, and instrument operation for continuous-wave and FT-NMR have been
made to contrast more sharply. A number of NMR spectra, with suggestions on pre-
sentation of the data, and basic interpretation have also been added.
Presentation of a more modern outline of the instrumentation of HPLC
( Chapter 31) includes discussion of automatic injectors, yet there is a bit of a loss
as this instrument, now highly computer-controlled, no longer has visible pumps,
valves, and miles of tubing and fi ttings, just a series of fairly quiet, putty-colored
boxes that produce excellent data with ease and a bit of boredom.
This kind of transition has put this edition of the Survival Manual into a bit of
an “equilibrium mode,” as now, at the urging of reviewers, some older techniques
have been removed as newer information has been included. The actual making of
TLC plates on microscope slides, which apparently needs not be done anymore, has
been removed, and comments about handling and cutting pre-prepared plates have
been updated and expanded (Chapter 27).
I’d like to thank my reviewers, Sean O’Connor, Clemson University;
Lucy Moses, Virginia Commonwealth University; Christine Rich, University of
L ouisville; Sean O’Connor, University of New Orleans; Jeffrey Hugdahl, Mercer
University; Kathleen Peterson, University of Notre Dame; Chavonda Mills, Georgia
College & State University; Beatrix Aukszi, Nova Southeastern University; Robert
Stockland, Bucknell University; Jennifer Krumper, UNC-Chapel Hill; Rui Zhang,
Western Kentucky University; Holly Sebahar, University of Utah; Adam List,
Vanderbilt University for their comments and suggestions, most of which have been
iii
iv PREFACE TO THE NINTH EDITION
incorporated in this work. Finally, I’d like to thank Petra Recter, Associate Publisher,
Chemistry and Physics, for the chance to perform this update, and Joan Kalkut,
Sponsoring Editor, for her tremendous patience and support during a personally
diffi cult time.
J. W. Zubrick
Hudson Valley Community College
CONTENTS
CHAPTER 1 SAFETY FIRST, LAST, AND ALWAYS 1
Accidents Will Not Happen 5
Disposing of Waste 5
Mixed Waste 7
Material Safety Data Sheet (MSDS) 8
Green Chemistry and Planning an Organic Synthesis 9
An iBag for Your iThing 10
Exercises 10
CHAPTER 2 KEEPING A NOTEBOOK 11
A Technique Experiment 12
Notebook Notes 13
A Synthesis Experiment 13
Notebook Notes 13
Calculation of Percent Yield (Not Yeild!) 23
Estimation Is Your Friend 25
The Acid Test 25
Notebook Mortal Sin 25
Exercises 26
CHAPTER 3 INTERPRETING A HANDBOOK 27
CRC Handbook 28
Entry: 1-Bromobutane 28
Entry: Benzoic Acid 29
Lange’s 31
Entry: 1-Bromobutane 31
Entry: Benzoic Acid 31
Merck Index 31
Entry: 1-Bromobutane 33
Entry: Benzoic Acid 34
There’s a CD 34
The Aldrich Catalog 35
Entry: 1-Bromobutane 35
Entry: Benzoic Acid 36
Not Clear–Clear? 36
Info on the Internet 37
Exercises 37
v
vi CONTENTS
CHAPTER 4 JOINTWARE 38
Stoppers with Only One Number 39
Another Episode of Love of Laboratory 40
Hall of Blunders and Things Not Quite Right 42
Round-Bottom Flasks 42
Columns and Condensers 43
The Adapter with Lots of Names 43
Forgetting the Glass 45
Inserting Adapter Upside Down 45
Inserting Adapter Upside Down sans Glass 46
The O-Ring and Cap Branch Out 46
Greasing the Joints 46
To Grease or Not to Grease 47
Preparation of the Joints 47
Into the Grease Pit 47
Storing Stuff and Sticking Stoppers 48
Corking a Vessel 48
CHAPTER 5 MICROSCALE JOINTWARE 50
Microscale: A Few Words 51
Uh-Oh Rings 51
The O-Ring Cap Seal 51
Skinny Apparatus 51
Not-So-Skinny Apparatus 52
Sizing Up the Situation 52
Why I Don’t Really Know How Vacuum-Tight These Seals Are 54
The Comical Vial (That’s Conical!) 54
The Conical Vial as Vial 55
Packaging Oops 55
Tare to the Analytical Balance 55
The Electronic Analytical Balance 56
Heating These Vials 56
The Microscale Drying Tube 57
Gas Collection Apparatus 58
Generating the Gas 59
Isolating the Product 61
CHAPTER 6 OTHER INTERESTING EQUIPMENT 62
Funnels, and Beakers, and Flasks—Oh My! 63
The Flexible Double-Ended Stainless Steel Spatula 63
CONTENTS vii
CHAPTER 7 PIPET TIPS 66
Pre-Preparing Pasteur Pipets 67
Calibration 68
Operation 68
Amelioration 68
Pipet Cutting 70
Pipet Filtering—Liquids 70
Pipet Filtering—Solids 71
CHAPTER 8 SYRINGES, NEEDLES, AND SEPTA 73
The Rubber Septum 75
CHAPTER 9 CLEAN AND DRY 77
Drying Your Glassware When You Don’t Need To 78
Drying Your Glassware When You Do Need To 79
CHAPTER 10 DRYING AGENTS 80
Typical Drying Agents 81
Using a Drying Agent 82
Following Directions and Losing Product Anyway 82
Drying Agents: Microscale 83
Drying in Stages: The Capacity and Effi ciency of Drying Agents 83
Exercises 83
CHAPTER 11 ON PRODUCTS 84
Solid Product Problems 85
Liquid Product Problems 85
The Sample Vial 85
Hold It! Don’t Touch That Vial 86
CHAPTER 12 THE MELTING-POINT EXPERIMENT 87
Sample Preparation 88
Loading the Melting-Point Tube 89
Closing Off Melting-Point Tubes 90
Melting-Point Hints 90
The Mel-Temp Apparatus 91
Operation of the Mel-Temp Apparatus 92
The Fisher-Johns Apparatus 93
Operation of the Fisher-Johns Apparatus 94
The Thomas-Hoover Apparatus 95
Operation of the Thomas-Hoover Apparatus 97
viii CONTENTS
Using the Thiele Tube 99
Cleaning the Tube 100
Getting the Sample Ready 101
Dunking the Melting-Point Tube 102
Heating the Sample 103
Exercises 103
CHAPTER 13 RECRYSTALLIZATION 104
Finding a Good Solvent 105
General Guidelines for a Recrystallization 106
My Product Disappeared 107
Gravity Filtration 107
The Buchner Funnel and Filter Flask 110
Just a Note 113
The Hirsch Funnel and Friends 113
Activated Charcoal 114
The Water Aspirator: A Vacuum Source 114
The Water Trap 115
Working with a Mixed-Solvent System—The Good Part 115
The Ethanol–Water System 116
A Mixed-Solvent System—The Bad Part 116
Salting Out 117
World-Famous Fan-Folded Fluted Paper 118
Exercises 119
CHAPTER 14 RECRYSTALLIZATION: MICROSCALE 120
Isolating the Crystals 121
Craig Tube Filtration 122
Centrifuging the Craig Tube 124
Getting the Crystals Out 125
CHAPTER 15 EXTRACTION AND WASHING 127
Never-Ever Land 128
Starting an Extraction 129
Dutch Uncle Advice 130
The Separatory Funnel 131
The Stopper 131
The Glass Stopcock 131
The Tefl on Stopcock 132
How to Extract and Wash What 134
The Road to Recovery—Back-Extraction 135
A Sample Extraction 136
Performing an Extraction or Washing 137
Extraction Hints 139
Exercises 140
