er!™ g Everything Easi Makin If you’re feeling challenged by organic chemistry, fear not! This easy-to-understand guide explains the basic principles in simple terms, providing insight into the language of organic chemists, the major classes of compounds, and more. Complete with new explanations and example equations, this book will help you ace your organic chemistry class! • Go organic — get an introduction to organic chemistry, from dissecting atoms and the basics of bases and acids, to stereochemistry and drawing structures • Hydrocarbons — dive into hydrocarbons, including a full explanation of alkanes, alkenes, and alkynes • Functional groups — understand substitution and elimination reactions, the alcohols, conjugated alkenes, aromatic compounds, and much more • A smashing time — find out about mass spectrometry, IR spectroscopy, NMR spectroscopy, solving problems in NMR, and more Open the book and find: • Tips on deciphering “organic speak” • How to determine the structure of a molecule • A complete overview of chemical reactions • Strategies for solving organic chemistry problems • Tricks to prepare for organic chemistry exams • Renewed example equations in this new edition • New explanations and practical examples Organic Chemistry I The fun and easy way to take the confusion out of organic chemistry 2nd Edition Cover Image: ©cb34inc/iStockphoto.com Arthur Winter is a graduate of Frostburg State University, where he received his BS in chemistry. Winter received his PhD at the University of Maryland in 2007, where his research involved studying extremely short-lived reactive intermediates using laser spectroscopy. He is currently a chemistry professor at Iowa State University. rganic O mistry I Che Learn to: • Survive organic chem — get tips on surviving your organic chemistry class, along with information on cool organic discoveries, and ten of the greatest organic chemists • Grasp the principles of organic chemistry at your own pace • Score your highest in your Organic Chemistry I course Go to Dummies.com® for videos, step-by-step examples, how-to articles, or to shop! • Decipher organic reactions $22.99 USA / $27.99 CAN / £16.99 UK ISBN:978-1-118-82807-6 52299 Arthur Winter, PhD 9 781118 828076 Winter 2nd Edition Chemistry professor and author of Organic Chemistry I Workbook For Dummies®
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Chemistry I 2nd Edition
Chemistry I 2nd Edition by Arthur Winter, PhD
, Published by: John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030-5774, www.wiley.com Copyright © 2014 by John Wiley & Sons, Inc., Hoboken, New Jersey Published simultaneously in Canada 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 the prior written permission of the Publisher. Requests to the Publisher for permission should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, (201) 748-6011, fax (201) 748-6008, or online at http://www.wiley.com/go/permissions. Trademarks: Wiley, For Dummies, the Dummies Man logo, Dummies.com, Making Everything Easier, and related trade dress are trademarks or registered trademarks of John Wiley & Sons, Inc., and may not be used without written permission. All other trademarks are the property of their respective owners. John Wiley & Sons, Inc., is not associated with any product or vendor mentioned in this book. LIMIT OF LIABILITY/DISCLAIMER OF WARRANTY: WHILE THE PUBLISHER AND AUTHOR HAVE USED THEIR BEST EFFORTS IN PREPARING THIS BOOK, THEY MAKE NO REPRESENTATIONS OR WARRANTIES WITH RESPECT TO THE ACCURACY OR COMPLETENESS OF THE CONTENTS OF THIS BOOK AND SPECIFICALLY DISCLAIM ANY IMPLIED WARRANTIES OF MERCHANTABILITY OR FITNESS FOR A PARTICULAR PURPOSE. NO WARRANTY MAY BE CREATED OR EXTENDED BY SALES REPRESENTATIVES OR WRITTEN SALES MATERIALS. THE ADVISE AND STRATEGIES CONTAINED HEREIN MAY NOT BE SUITABLE FOR YOUR SITUATION. YOU SHOULD CONSULT WITH A PROFESSIONAL WHERE APPROPRIATE. NEITHER THE PUBLISHER NOR THE AUTHOR SHALL BE LIABLE FOR DAMAGES ARISING HEREFROM. For general information on our other products and services, please contact our Customer Care Department within the U.S. at 877-762-2974, outside the U.S. at 317-572-3993, or fax 317-572-4002. For technical support, please visit www.wiley.com/techsupport. Wiley publishes in a variety of print and electronic formats and by print-on-demand. Some material included with standard print versions of this book may not be included in e-books or in print-on-demand. If this book refers to media such as a CD or DVD that is not included in the version you purchased, you may download this material at http://booksupport.wiley.com. For more information about Wiley products, visit www.wiley.com. Library of Congress Control Number: 2013954080 ISBN 978-1-118-82807-6 (pbk); ISBN 978-1-118-82796-3 (ebk); ISBN 978-1-118-82813-7 (ebk) Manufactured in the United States of America 10 9 8 7 6 5 4 3 2 1
Introduction................................................................. 1 Part I: Getting Started with Organic Chemistry............... 5 Chapter 1: The Wonder ul World of Organic Chemistry............................................... 7 f Chapter 2: Dissecting Atoms: Atomic Structure and Bonding.................................... 15 Chapter 3: Speaking with Pictures: Drawing Structures.............................................. 35 Chapter 4: Covering the Bases (And the Acids)........................................................... 59 Chapter 5: Reactivit Centers: Functional Groups....................................................... 69 y Chapter 6: Seeing in 3-D: Stereochemistr .................................................................... 85 y Part II: Hydrocarbons............................................... 103 Chapter 7: What’s in a Name? Alkane Nomenclature................................................. 105 Chapter 8: Drawing Alkanes.......................................................................................... 113 Chapter 9: Seeing Double: The Alkenes....................................................................... 129 Chapter 10: Reactions of Alkenes................................................................................. 145 Chapter 11: It Takes Alkynes: The Carbon-Carbon Triple Bond............................... 159 Part III: Functional Groups........................................ 167 Chapter 12: Replacing and Removing: Substitution and Elimination Reactions.................................................................................................. 169 Chapter 13: Getting Drunk on Organic Molecules: The Alcohols............................. 185 Chapter 14: Side-by-Side: Conjugated Alkenes and the Diels–Alder Reaction.................................................................................................... 193 Chapter 15: Lord of the Rings: Aromatic Compounds............................................... 203 Chapter 16: Bringing Out the Howitzers: Reactions of Aromatic Compounds....... 221 Part IV: Spectroscopy and Structure Determination..... 235 Chapter 17: A Smashing Time: Mass Spectrometry................................................... 237 Chapter 18: Seeing Good Vibrations: IR Spectroscopy.............................................. 255 Chapter 19: NMR Spectroscopy: Hold onto Your Hats, You’re Going Nuclear!...... 267 Chapter 20: Following the Clues: Solving Problems in NMR..................................... 289
Chapter 21: Ten (Or So) Great Organic Chemists...................................................... 311 Chapter 22: Ten Cool Organic Discoveries.................................................................. 317 Chapter 23: Ten Cool Organic Molecules.................................................................... 325 Part VI: Appendixes.................................................. 331 Appendix A: Working Multistep Synthesis Problems................................................ 333 Appendix B: Working Reaction Mechanisms.............................................................. 341 Appendix C: Glossary..................................................................................................... 347 Index....................................................................... 359
Introduction.................................................................. 1 About This Book............................................................................................... 2 Foolish Assumptions........................................................................................ 3 Icons Used in This Book.................................................................................. 3 Beyond the Book.............................................................................................. 4 Where to Go from Here.................................................................................... 4 Part I: Getting Started with Organic Chemistry................ 5 Chapter 1: The Wonder ful World of Organic Chemistry . . . . . . . . . . . . . 7 Shaking Hands with Organic Chemistry........................................................ 7 What Are Organic Molecules, Exactly?.......................................................... 9 An Organic Chemist by Any Other Name . . ............................................... 10 Synthetic organic chemists................................................................. 11 Bioorganic chemists............................................................................. 11 Natural products chemists.................................................................. 12 Physical organic chemists................................................................... 13 Organometallic chemists..................................................................... 13 Computational chemists...................................................................... 13 Materials chemists................................................................................ 14 Chapter 2: Dissecting Atoms: Atomic Structure and Bonding . . . . . . . 15 Electron House Arrest: Shells and Orbitals................................................. 16 Electron apartments: Orbitals............................................................. 17 Electron instruction manual: Electron configuration...................... 19 Atom Marriage: Bonding................................................................................ 20 To Share or Not to Share: Ionic and Covalent Bonding............................. 21 Mine! They’re all mine! Ionic bonding................................................ 21 The name’s Bond, Covalent Bond....................................................... 22 Electron piggishness and electronegativity...................................... 23 Separating Charge: Dipole Moments............................................................ 25 Problem solving: Predicting bond dipole moments......................... 26 Problem solving: Predicting molecule dipole moments.................. 26 Seeing Molecular Geometries....................................................................... 28 Mixing things up: Hybrid orbitals....................................................... 28 Predicting hybridization for atoms.................................................... 31 It’s All Greek to Me: Sigma and Pi Bonding................................................. 32
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