DOCUMENT RESUME ED 477 260 SE 067 621 AUTHOR Jarvis, Bruce; Mazzocchi, Paul TITLE Form and Function: An Organic Chemistry Module. ISBN ISBN-06-561122-5 PUB DATE 1978-00-00 NOTE 147p.; Produced by the Chemistry Association of Maryland. For Teacher's Guide, see SE 067 622. For other modules in series, see SE 067 618-630. PUB TYPE Books (010) Guides Classroom Learner (051) EDRS PRICE EDRS Price MF01/PC06 Plus Postage. DESCRIPTORS Curriculum Design; *Instructional Materials; *Interdisciplinary Approach; *Organic Chemistry; Science Instruction; Secondary Education ABSTRACT This book is one in the series of Interdisciplinary Approaches to Chemistry (IAC) designed to help students discover that chemistry is a lively science and actively used to pursue solutions to the important problems of today. It is expected for students to see how chemistry takes place continuously all around and to readily understand the daily problems facing them and their environment. Contents include: (1) "Organic Chemistry"; (2) "Hydrocarbons"; (3) "Reactions of Hydrocarbons"; (4) "Alcohols: Oxidized Hydrocarbons"; (5) "Poisons and Chemical Warfare"; (6) "Aldehydes and Ketones";(7) "Pesticides and Sex Attractants";(8) "Esters and Acids";(9) "Organic Bases: The Amines";(10) "Polymers: The Linking of Molecules";(11) "Photochemistry: Light and Heat"; and (12)"Drugs: From Aspirin to Hallucinogens". (KHR) Reproductions supplied by EDRS are the best that can be made from the original document. interdisciplinary approaches U.S. DEPARTMENT OF EDUCATION Office of Educational Research and Improvement g030A121217g PERMISSION TO REPRODUCE AND DISSEMINATE THIS MATERIAL HAS EDUCATIONAL RESOURCES INFORMATION BEEN GRANTED BY CENTER (ERIC) Ls.ciecument has been reproduced as received from the person or organization originating it. C, 0 Minor changes have been made to N improve reproduction quality. TO THE EDUCATIONAL RESOURCES Points of view or opinions stated in this N INFORMATION CENTER (ERIC) document do not necessarily represent 1 official OERI position or policy. N ORGANO© CHEMOSTRY MODULE - 3327 COPY MAMA THIS BOOK IS THE P OPERTY OF STATE Book No. PROVINCE COUNTY Enter information in spaces PARISH SCHOOL DISTRICT to the left as OTHER instructed CONDITION Year ISSUED TO Used ISSUED RETURNED PUPILS to whom this textbook is issued must not write on any page or mark any part of it in any way, consumable textbookp excepted. 1. Teachers should see that the pupil's name is clearly written in ink in the spaces above in every book issued. 2. The following terms should be used in recording the condition of the book: New; Good; Fair; Poor; Bad. interdisciplinary approaches 40lacto chemistry FORM AND FUNCTION AN ORGANIC CHEMISTRY MODULE Bruce Jarvis Paul Mazzocchi 1817 Harper & Row, Publishers New YorkHagerstownSan FranciscoLondon interdisciplinary IAC PROJECT TEAM approaches to chemistry Directors of IAC: Marjorie Gardner, 1971-73, 1976 Henry Heikkinen, 1973-76 lac Revision Coordinator: Alan DeGennaro IAC MODULAR CHEMISTRY PROGRAM MODULE AUTHORS REACTIONS AND REASON: Gordon Atkinson, Henry Heikkinen An Introductory Chemistry Module DIVERSITY AND PERIODICITY: James Huheey An Inorganic Chemistry Module FORM AND FUNCTION: Bruce Jarvis, Paul Mazzocchi An Organic Chemistry Module MOLECULES IN LIVING SYSTEMS: David Martin, Joseph Sampugna A Biochemistry Module THE HEART OF MATTER: Vic Viola A Nuclear Chemistry Module THE DELICATE BALANCE: Glen Gordon, William Keifer An Energy and the Environment Chemistry Module COMMUNITIES OF MOLECULES: Howard DeVoe A Physical Chemistry Module Teacher's Guides Teacher's Guide Coordinators: (available for each module) Robert Hearle, Amado Sandoval 1981 Printing Copyright © 1978 by Chemistry Associates of Maryland, Inc. All rights reserved. Printed in the United States of America. No part of this publication may be reproduced in any form or by any means, photographic, electrostaticor mechanical, or by any information storage and retrieval system or other method, for any use, without written permission from the publisher. STANDARD BOOK NUMBER 06-561122-5 12MU09876543 1 i AUTHORS FORM AND FUNCTION: AN ORGANIC CHEMISTRY MODULE Bruce Jarvis and Paul Mazzocchi BRUCE JARVIS Bruce Jarvis arrived at the University of Maryland in 1967, and many people feel that the chemistry department will never be the same again. Sometimes embarrassing to his older colleagues, his graphic explanations during classes and seminars (they have, at times, taken the form of short, costumed one-act plays) are eagerly awaited by his students and coworkers. The exuberance and inquiring mind of Bruce Jarvis have brought a new dimension to chemistry research and teaching activities at the university. PAUL MAZZOCCHI Paul Mazzocchi came to the University of Maryland in 1967. Since then he has established himself in the chemistry department not only as a good scientist and teacher (winner of the university's Ex- cellence in Teaching Award) but also as a master storyteller. As a young boy growing up on the streets of New York, "Mazzoc" rapidly learned to cope with all of the vagaries of life. More mature now, he continues to bring to the chemistry classroom a certain wisdom, understanding, and humor that go beyond the subject itself. III ". ATOMYRIADES NATURE, it seems, is the popular name for milliards and milliards and milliards of particles playing their infinite game of billiards and billiards and billiards. Piet Hein © 1966 by Piet Hein PREFACE Welcometo IAC Chemistry. Enjoy this year as you explore this important area of science. Chemistry is to be enjoyed, cultivated, comprehended. It is part of our culture, of our everyday lives. Polymers, paints, pharmaceuticals, people, and pollution all have something in commona chemical base. IAC Chemistry is relevant, interdisciplinary,student centered, and filled with important concepts and processes. IAC will help you discover that chemistry is a lively science and being actively used to pursue solutions to the important problems of today. You will see how chemistry is taking place continuously all around. You will more readily understand the daily problems facing you and your environment. Students throughout this country and in a number of other countries as well have let us know that they like and learn from the IAC modules. Classroom teachers have suggested changes to make them even better. Since the IAC authors believe that student involvement in chem- I'D LIKE I'd like to know istry is very important, there are many activities that allow you to what this whole show develop and apply chemistry concepts directly. We have tried to is all about make the modules flexible, easy to read, and enjoyable, discussing before its out. (4) everyday problems and adding a bit of humor that may help you Piet Hein remember some of the more important ideas. The Time Machines are intended to give you a sense of when the more important discoveries in chemistry happened in relation to other events. Wonderinquire--investigate. Think through all that you find here. But most of allenjoy chemistry as you learn about the atoms, molecules, elements, and compounds that make up your universe. IAC is written for your learning pleasure. © 1966 by Piet Hein *Piet Hein is a Scandinavian poet who often Marjorie Gardner served as a "mental Ping-Pong partner" forDirector the famous chemist Niels Bohr. Interdisciplinary Approaches to Chemistry iv Contents Preface iv ORGANIC CHEMISTRY 1 0-1 A Vital Force? 2 0-2 Diversity of Organic Molecules 3 0-3 Carbon's Covalent Bonds 4 HYDROCARBONS 5 0-4 Energy: From the Sun to You 6 0-5 Fossil Fuels: Stored Organic Energy 7 0-6 Energy Plus Problems 8 0-7 The Single-Bonded Alkanes 12 0-8 Straight-Chain Molecular ModelsIMiniexperiment 13 0-9 Branched-Chain Molecular Models/Miniexperiment 14 0-10 Comparing Pro perties/Miniexperiment 15 0-11Fuels: How Well Do They Burn? 15 0-12 Separating Hydrocarbons 18 0-13Fractional Distillation/Experiment 21 REACTIONS OF HYDROCARBONS 22 0-14 How Strong the Bond That Binds 23 0-15 Chains and Rings 25 0-16 The Benzene Ring 26 0-17Reactions of HydrocarbonslMiniexperiment 28 0-18Fused Rings: Bigger but Not Better 28 0-19 Molecules with a Bang 29 ALCOHOLS: OXIDIZED HYDROCARBONS 33 0-20Oxidation and Reduction 34 0-21 Methyl and Ethyl: Their Properties 35 0-22 Another Type of Bonding 36 0-23Functional Groups: Focus of the Matter 37 0-24 Fermented and Distilled Alcohols 39 0-25 Comparing Solubilities/Experiment 41 0-26Polyalcohols 42 a V POISONS AND CHEMICAL WARFARE 43 0-27Tears and More Tears 44 0-28Alkylating Agents 45 0-29 Nerve Gases 46 0-30 Chemical Warfare in the Animal World 47 ALDEHYDES AND KETONES 50 0-31 The Carbonyl Clan 51 0-32Carbonyl Chemistry and the Millipede 52 0-33 The Bombardier Beetle 54 PESTICIDES AND SEX ATTRACTANTS 57 0-34Insecticides: Chlorinated Hydrocarbons 58 0-35Chlorinated Hydrocarbon Problems 60 0-36 Ban All Insecticides? 61 0-37Sex Attractants: An Alternative 62 ESTERS AND ACIDS 66 0-38Preparation of Esters/Experiment 67 0-39Organic Acids 68 0-40Synthesis of Aspirin/Experiment 71 0-41Soaps and Detergents 72 0-42Preparation of SoaplExperiment 73 0-43 Maintaining the Cycle 76 ORGANIC BASES: THE AMINES 77 0-44 Ammonia's Offspring 78 0-45Molecular Nitrogen 79 9 vi POLYMERS: THE LINKING OF MOLECULES 84 0-46 The Making of Macromolecules 85 0-47 From Monomer to Polymer 86 0-48Synthesis of Nylon 66IExperiment 88 0-49Properties of Polymers 88 0-50Natural and Synthetic Polymers 91 0-51Mirror Image Molecular ModelslExperiment 96 PHOTOCHEMISTRY: LIGHT AND HEAT 98 0-52Cold Light: Its Sources 99 0-53 Chemiluminescence of LuminollExperiment 100 0-54Cold Light: Its Uses 100 0-55Chemistry of Vision 103 0-56Photochemical Reaction/Experiment 107 DRUGS: FROM ASPIRIN TO HALLUCINOGENS 108 0-57Let's Start with Aspirin 109 0-58Alkaloids 110 0-59Hallucinogens: The "Dream Makers" 112 0-60Marijuana: Psychoactive Plant 115 0-61Stimulants 117 0-62Narcotics: Analgesic but Addictive 119 0-63Barbiturates: The Synthetics 120 SUMMING UP 121 Appendix I: Safety 123 Appendix II: Nomenclature 124 Appendix III:Interesting Molecular Structures 127 Selected Readings 131 Acknowledgments 132 Index 134 Table of International Relative Masses 136 Periodic Table of the Elements 10 VII Organic Chemistry Look around you.