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Organic Chemistry I for Dummies Science/Chemistry/Organic Easier!™ Making Everything 2nd ition Ed 2nd Edition The fun and easy way Organic Chemistry I to take the confusion Open the book and find: out of organic chemistry • Tips on deciphering “organic speak” If you’re feeling challenged by organic chemistry, fear not! • How to determine the Organic This easy-to-understand guide explains the basic principles structure of a molecule in simple terms, providing insight into the language of • A complete overview of organic chemists, the major classes of compounds, and more. chemical reactions Complete with new explanations and example equations, this • Strategies for solving organic book will help you ace your organic chemistry class! Chemistry I chemistry problems • Go organic — get an introduction to organic chemistry, • Tricks to prepare for organic from dissecting atoms and the basics of bases and acids, chemistry exams to stereochemistry and drawing structures • Renewed example equations • Hydrocarbons — dive into hydrocarbons, including a full in this new edition explanation of alkanes, alkenes, and alkynes • New explanations and • Functional groups — understand substitution and elimination practical examples reactions, the alcohols, conjugated alkenes, aromatic compounds, and much more • A smashing time — find out about mass spectrometry, IR spectroscopy, NMR spectroscopy, solving problems Cover Image: ©cb34inc/iStockphoto.com in NMR, and more Learn to: • Survive organic chem — get tips on surviving your organic chemistry class, along with information on cool organic • Grasp the principles of organic discoveries, and ten of the greatest organic chemists chemistry at your own pace ® • Score your highest in your Arthur Winter is a graduate of Frostburg State University, where he Go to Dummies.com Organic Chemistry I course for videos, step-by-step examples, received his BS in chemistry. Winter received his PhD at the University how-to articles, or to shop! of Maryland in 2007, where his research involved studying extremely • Decipher organic reactions short-lived reactive intermediates using laser spectroscopy. He is currently a chemistry professor at Iowa State University. $22.99 USA / $27.99 CAN / £16.99 UK ISBN:978-1-118-82807-6 52299 Arthur Winter, PhD Chemistry professor and author of Organic 9 781118 828076 Winter Chemistry I Workbook For Dummies® Get More and Do More at Dummies.com® Start with FREE Cheat Sheets Cheat Sheets include • Checklists • Charts • Common Instructions • And Other Good Stuff! To access the Cheat Sheet created specifically for this book, go to www.dummies.com/cheatsheet/organicchemistry Get Smart at Dummies.com Dummies.com makes your life easier with 1,000s of answers on everything from removing wallpaper to using the latest version of Windows. 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Organic Chemistry I 2nd Edition Organic Chemistry I 2nd Edition by Arthur Winter, PhD Organic Chemistry I For Dummies®, 2nd Edition 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. 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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 Contents at a Glance Introduction ................................................................ 1 Part I: Getting Started with Organic Chemistry .............. 5 Chapter 1: The Wonder ful World of Organic Chemistry ..............................................7 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 y Centers: Functional Groups ......................................................69 Chapter 6: Seeing in 3-D: Stereochemistr y ...................................................................85 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 Part V: The Part of Tens ........................................... 309 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 Table of Contents
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