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Full text of ' 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 107 and 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. Chemistry, Organic — Laboratory manuals.

QD261.Z83 1988 547'.008 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 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, 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 recrystalliza- tion solvent. Once their samples are purified, students may now find direc- tions for taking a melting point with the Thomas -Hoover apparatus. Wash- ing 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 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 distilla- tion. 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 Clausius- Clapyron 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 sugges- tions while working in the laboratory. A special thanks to Professor G.J. Janz, director of the Molten Salts Data Center at the Rensselaer Polytechnic Insti- tute 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 viii PREFACE TO THE SECOND EDITION 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 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. Dawn Reitz, Produc- tion Supervisor, Ms.

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Ann Meader, Supervising Copy Editor, and Mr. Glenn Petry, Copy Editor deserve a great deal of credit in bringing this second edition about. Zubrick Hudson Valley Community College April 3, 1987 Preface to the First Edition Describe, for the tenth time, an instrument not covered in the laboratory book, and you write a procedure. Explain, again and again, operations that are in the book, and you get a set of notes. When these produce questions you revise until the students, not you, finally have it right.

Zubrick Organic Chem Lab Survival Manual

It you believe that writing is solidified speech — with the same pauses, the same cadences — then a style is set. And if you can still laugh, you write this book. This book presents the basic techniques in the organic chemistry labora- tory with the emphasis of doing the work correctly the first time.

To this end, examples of what can go wrong are presented with admonishments, often bordering on the outrageous, to forestall the most common of errors. This is done in the belief that it is much more difficult to get into impossible experi- mental troubles once the student has been warned of the merely improbable ones. Complicated operations, such as distillation and extraction, are dealt with in a straightforward fashion, both in the explanations and in the se- quential procedures. The same can be said for the sections concerning the instrumental tech- niques of GC, IR, NMR, and HPLC. The chromatographic techniques of GC and HPLC are presented as they relate to thin-layer and column chromatog- raphy.

The spectroscopic techniques depend less on laboratory manipulation and so are presented in terms of similarities to the electronic instrumentation of GC and HPLC techniques (dual detectors, UV detection in HPLC, etc.). For all techniques, the emphasis is on correct sample preparation and correct instrument operation.

Many people deserve credit for their assistance in producing this textbook. It has been more than a few years since this book was first written, and a list of acknowledgements would approach the size of a small telephone directory — there are too many good people to thank directly.

For those who encouraged, helped, and constructively criticized, thanks for making a better book that students enjoy reading and learning from. I'd like to thank the hundreds of students who put up with my ravings, rantings, put-ons, and put-downs, and thus taught me what it was they needed to know, to survive organic chemistry laboratory. A special thanks to Dr. Schimelpfenig, for encouragement over many years when there was none, and whose comments grace these pages; Dr. Carson, whose comments also appear, for his useful criticism concerning the x PREFACE TO THE FIRST EDITION presentation; Drs.

Bunce, and H.B. Hollinger for their constant support and suggestions; Dr. Freilich, whose viewpoint as an inorganic chemist proved valuable during the review of manuscript; and Dr. Sam Johnson, who helped enormously with the early stages of the text processing. I also thank Christopher J. Kemper and Keith Miller for their valuable comments on the instrumental sections of the book.

Finally, I'd like to thank Clifford W. Mills, my patron saint at John Wiley & Sons, without whose help none of this would be possible, and Andrew E. Ford, Jr., vice president, for a very interesting start along this tortured path to publication. Some Notes on Style It is common to find instructors railing against poor usage and complaining that their students cannot do as much as to write one clear, uncomplicated, communicative English sentence. Yet I am astonished that the same people feel comfortable with the long and awkward passive voice, the pompous 'we' and the clumsy 'one,' and that damnable 'the student,' to whom exercises are left as proofs.

These constructions, which appear in virtually all scientific texts, do not produce clear, uncomplicated, communi- cative English sentences. And students do learn to write, in part, by following example. I do not go out of my way to boldly split infinitives, nor do I actively seek prepositions to end sentences with. Yet by these constructions alone, I may be viewed by some as aiding the decline in students' ability to communicate. White, in the second edition of The Elements of Style (Macmillan, New York, 1972, p.

70), writes Years ago, students were warned not to end a sentence with a preposi- tion; time, of course, has softened that rigid decree. Not only is the preposition acceptable at the end, sometimes it is more effective in that spot than anywhere else. 'A claw hammer, not an axe, was the tool he murdered her with.' This is preferable to 'A claw hammer, not an ax, was the tool with which he murdered her.'

Some infinitives seem to improve on being split, just as a stick of round stovewood does. 'I cannot bring myself to really like the fellow.' The sentence is relaxed, the meaning is clear, the violation is harmless and scarcely perceptible. Put the other way, the sentence becomes stiff, need- lessly formal. A matter of ear. We should all write as poorly as White.

With the aid of William Strunk and E.B. White in The Elements of Style and that of William Zinsser in On Writing Well, Rudolph Flesch in The ABC of Style, and D.L.

Carson, whose comments appear in this book, I have tried to follow some principles of technical communication lately ignored in scientific texts: use the first person, put yourself in the reader's place, and, the best for last, use the active voice and a personal subject. Xii SOME NOTES ON STYLE The following product names belong to the respective manufacturers. Regis- tered trademarks are indicated here, as appropriate; in the text, the symbol is omitted. Corning Glass Works, Corning, New York W. Hammond Drierite Company, Xenia, Ohio Fisher Scientific Company, Pittsburgh, Pennsylvania Becton, Dickinson and Company, Rutherford, New Jersey Laboratory Devices, Cambridge, Massachusetts Millipore Corporation, Bedford, Massachusetts Crawford Fitting Company, Solon, Ohio E.I. DuPont de Nemours & Company, Wilmington, Delaware Variac® General Radio Company, Concord, Massachusetts Corning® Drierite® Fisher-Johns® Luer-Lok® Mel-Temp® Millipore® Swagelok® Teflon® Forewords Seldom does one have the opportunity to read and use a textbook that is completely useful, one that does not need substitutions and deletions. Zu- brick's book is this type of resource for undergraduate organic students and their laboratory instructors and professors.

I must heartily recommend this book to any student taking the first laboratory course in organic chemistry. The Organic Chem Lab Survival Manual is filled with explanations of necessary techniques in much the same way that advanced techniques have been presented in books by Wiberg, Lowenthal, Newman, and Gordon and Ford. In larger universities, The Survival Manual is a valuable supplement to most laboratory manuals. It provides explanations that many graduate teaching assistants do not take time to give to their classes. Most teaching assistants of my acquaintance appreciate Zubrick's book because it supports their discussions during recitations (when each student has a personal copy), and it refreshes their memories of good techniques they learned and must pass on to a new generation of undergraduates.

The book is addressed to the undergraduate student audience. The infor- mal tone appeals to most laboratory students. The illustrations are delightful. The use of different type fonts is effective for emphasis. Also, Zubrick always explains why the particular sequence of operations is necessary, as well as how to manipulate and support the apparatus and substances. This is a definite strength.

This book is an evolutionary product: Over the span of a decade, professors at major universities and liberal arts colleges have made suggestions for minor changes and improvements. I count myself fortunate to have used the forerunners, which have been published since 1973. A large quantity of useful information has been collected, well organized, and presented with great care.

Organic Chem Lab Survival Manual Exercise Answers

This book is the handiwork of a master teacher. Schimelpfenig Dallas Baptist University Dallas, Texas The Organic Chem Lab Survival Manual is a book I have known about for a number of years in a variety of developmental stages. As it progressed, I watched with interest as Jim Zubrick struggled to achieve a balance between merely conveying information — what most books do — and conveying that xiv FOREWORDS information efficiently to its very human audience. On the one hand, Jim insisted that his book contain all the necessary scientific detail; on the other hand, he also insisted that a 'how to' book for organic chemistry lab need not be written in the dull and confusing prose which so often passes as the lingua franca of science.

This book demonstrates that he has achieved both goals in admirable fashion. In fact, The Survival Manual succeeds very well in following Wittgenstein's dictum that 'everything that can be thought at all, can be thought clearly.

Organic Chem Lab Survival Manual Edition: 9th

Anything that can be said can be said clearly.' It also follows the advice of Samuel Taylor Coleridge to avoid pedantry by using only words 'suitable to the time, place, and company.' Although some few readers may take umbrage with this book because it is not, atypically couched in the language of a typical journal article, similar people no doubt also complained when William Strunk published Elements of Style in 1919.

For Strunk also broke with tradition. Most other writing texts of the day were written in the convoluted language of the nineteenth century, and the material they contained consisted largely of lists of arcane practices, taboos, and shibboleths — all designed to turn students into eighteenth-cen- tury writers. From Strunk's point of view, such texts were less than desirable for several major reasons. First, the medicine they offered students had little to do with the communication process itself; second, it had little to do with current practice; and third, taking the medicine was so difficult that the cure created more distress in the patients than did the disease itself.

Jim Zubrick proves in this book that he understands, as did Strunk, that learning reaches its greatest efficiency in situations where only that informa- tion is presented which is directly related to completing a specific task. In an environment fraught with hazards, efficiency of this sort becomes even more necessary. The Survival Manual is an excellent book because it speaks to its audience's needs. Always direct — if sometimes slightly irreverent — the book says clearly what many other books only manage to say with reverent indirection. It never forgets that time is short or that the learning curve rises very slowly at first. The prose is straightforward, easy to understand, and is well supported by plentiful illustrations keyed to the text. It is also technically accurate and technically complete, but it always explains matters of laboratory technology in a way designed to make them easily understandable to students in a func- tional context.

All of these characteristics related to communication efficiency will natu- FOREWORDS xv rally make the laboratories in which the book is used safer labs; the improved understanding they provide serves as natural enhancement to the book's emphatic and detailed approach to laboratory safety. Most important, however, all the elements of The Survival Manual come together in focusing on the importance of task accomplishment in a way which demonstrates the author's awareness that communication which does not efficiently meet the needs of its audience is little more than pedantry unsuitable to the time, place, and company. Carson Director, The Master of Science Program in Technical Communication Rensselaer Polytechnic Institute Contents 1.

Safety First, Last, and Always 1 Accidents Will Not Happen 5 2. Keeping A Notebook 7 A Technique Experiment 9 Notebook Notes 9 A Synthesis Experiment 9 Notebook Notes 13 3. Interpreting A Handbook 21 CRC Handbook 22 Entry: 1-Bromobutane 22 Entry: Benzoic Acid 25 Nostalgia 25 Lange's 27 Entry: 1-Bromobutane 28 Entry: Benzoic Acid 30 Merck Index 32 Entry: 1-Bromobutane 32 Entry: Benzoic Acid 33 The Aldrich Catalog 35 Entry: 1-Bromobutane 36 Entry: Benzoic Acid 37 Not Clear — Clear? Jointware 39 Stoppers with Only One Number 40 Another Episode of Love of Laboratory 41 Hall of Blunders and Things Not Quite Right 44 Round-Bottom Flasks 44 Columns and Condensers 44 The Adapter With Lots of Names 45 Forgetting The Glass 47 xviii CONTENTS Inserting Adapter Upside Down Inserting Adapter Upside Down Sans Glass Greasing the Joints To Grease or Not To Grease 48 49 49 49 Preparation of the Joints Into the Grease Pit 50 50 Storing Stuff and Sticking Stoppers Corking a Vessel The Cork Press 50 52 53 5. Other Interesting Equipment 55 6. Clean and Dry 59 Drying Your Glassware When You Don't Need To 60 Drying Your Glassware When You Need To 61 7.

Drying Agents 63 Typical Drying Agents 64 Using a Drying Agent 65 Following Directions and Losing Product Anyway 66 8. On Products 67 Solid Products 68 Liquid Products 68 The Sample Vial 69 Hold It! Don't Touch that Vial 69 9. The Melting Point Experiment 71 Sample Preparation 73 Loading the Melting Point Tube 73 Closing Off Melting Point Tubes 75 Melting Point Hints 75 The Mel-Temp Apparatus 76 Operation of the Mel-Temp Apparatus 77 The Fisher- Johns Apparatus 78 Operation of the Fisher - Johns Apparatus 79 The Thomas— Hoover Apparatus 80 CONTENTS xix Operation of the Thomas - Hoover Apparatus 82 Using the Thiele Tube 85 Cleaning the Tube 87 Getting the Sample Ready 87 Dunking the Melting Point Tube 87 Heating the Sample 88 10.

Recrystallization 91 Finding a Good Solvent 93 General Guidelines for a Recrystallization 94 Gravity Filtration 95 The Buchner Funnel and Filter Flask 98 Just a Note 100 Activated Charcoal 100 The Water Aspirator: A Vacuum Source 101 The Water Trap 102 Working with a Mixed-Solvent System — The Good Part 103 The Ethanol- Water System 103 A Mixed-Solvent System — The Bad Part 105 Salting-Out 106 World Famous Fan-Folded Fluted Filter Paper 107 1 1. Extraction and Washing 1 1 1 Never-Ever Land 113 Starting an Extraction 113 Dutch Uncle Advice 115 The Separatory Funnel 116 The Stopper 116 The Glass Stopcock 116 The Teflon Stopcock 118 The Stem 119 Washing and Extracting Various Things 120 How To Extract and Wash What 120 The Road to Recovery — Back-Extraction 122 A Sample Extraction 123 Performing an Extraction or Washing 125 Extraction Hints 127 XX 12. And Now— Boiling Stones 129 13. Sources of Heat 131 The Steam Bath 132 The Bunsen Burner 133 Burner Hints 135 The Heating Mantle 136 Proportional Heaters and Stepless Controllers 137 14. Clamps and Clamping 143 Clamping a Distillation Setup 146 15.

Ch 334 Syllabus Syllabus CH 334 Organic Chemistry Fall 2004 Instructor:, NS 112 Office Hours: MWF 9-10, W 10-11 Th 11-12 Office Telephone: (503) 838-8207 Email: Texts: Carey, 'Organic Chemistry', 5th Edition Study Guide to accompany Carey Rodig, et.al. 'Organic Chemistry Laboratory' Zubrick, 'The Organic Chem Lab Survival Manual Other Materials: Learning With Modeling CD-ROM (packaged with Carey Text) Bound Laboratory Manual with carbon copy pages Molecular Model Set Course Description: This course will cover the organic chemistry of alkanes, alkenes, and alkyl halides emphasizing their structures, properties, and reactions. The prerequisite for this course is successful completion of Ch 223 or consent of the instructor. Special Note: This is the first course in the year long organic chemistry sequence. Students completing the sequence will be required to take the American Chemical Society organic chemistry exam as the final exam for Ch 336. This is a standardized examination.

COURSE SCHEDULE Date Topic Text Reading Homework Problems (Text) Other Assignments 9/27 Bonding Ch 1: 1.1-1.9 1.33-1.40, 1.43, 1.44, 1.47, 1.53. GRADING SCALE MIDTERM EXAMS 2@100 pts 200 pts A: 500-465 pts B: 464-415 pts C: 414-365 pts D: 364-315 pts F: Below 315 pts QUIZZES 5@20 pts 100 pts FINAL EXAM 100 pts LABORATORY 100 pts TOTAL 500 pts QUIZZES: Short quizzes will be given on the days denoted by the symbol. Quizzes will be given promptly at 8 am. No makeup or late quizzes will be given.

The top 5 scores will be used in determining your grade. HOMEWORK: You are expected to have completed the reading assignment given for a particular date before coming to lecture on that date. The homework problems are intended to be completed after the lecture on the date listed. Working the assigned homework problems is essential to success in organic chemistry. These assignments will NOT be graded by the instructor. It is best to have read the textbook and studied the lecture material before attempting the homework assignments.

Try to work each problem as if it were a question on an examination. If you cannot answer the problem correctly, go back and reread the text and your lecture notes pertaining to the topic. Problems denoted by the symbol are molecular modeling exercises requiring a computer equipped with CD drive.

You will need to use the Molecular Modeling software on the CD-ROM bundled with your textbook to do these exercises. CLASS POLICIES:. It is your responsibility to be present at the times scheduled for exams. THERE WILL BE NO MAKEUP EXAMS GIVEN IN THIS COURSE. If you must miss an exam due to illness, your course grade will be determined by doubling the score on the final exam.

Cheating is a serious offense. If you cheat on any quiz, assignment or exam, the minimum penalty is a grade of zero for that work. Your conduct may also be referred to the Student Conduct Committee for assessment of a more severe penalty. Laboratory attendance is required.

There are no provisions for making up a missed laboratory experiment. The experiments must be performed during the scheduled time period. Note: At the end of Ch 336, students will take the American Chemical Society Organic Chemistry exam as the final.

This is a standardized, comprehensive exam used across the United States. The final exam for Ch 334 will cover all material presented during this term. The final exam must be taken at the time specified by the University calendar - DO NOT ask to take the final at another time!