Organic Chemistry I - download.e- Chemistry I For Dummies

  • View
    226

  • Download
    7

Embed Size (px)

Text of Organic Chemistry I - download.e- Chemistry I For Dummies

  • Organic Chemistry I

  • Organic Chemistry I

    2nd edition

    by Arthur Winter, PhD

  • Organic Chemistry I For Dummies, 2nd EditionPublished 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 978-1-119-29337-8 (pbk); ISBN 978-1-119-29656-0 (ebk); ISBN 978-1-119-29657-7 (ebk)

    Organic Chemistry I For Dummies, 2nd Edition (9781119293378) was previously published as Organic Chemistry I For Dummies, 2nd Edition (9781118828076). While this version features a new Dummies cover and design, the content is the same as the prior release and should not be considered a new or updated product.

    Manufactured in the United States of America

    10 9 8 7 6 5 4 3 2 1

    http://www.wiley.comhttp://www.wiley.com/go/permissionshttp://www.wiley.com/techsupporthttp://booksupport.wiley.comhttp://www.wiley.com

  • Contents at a GlanceIntroduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1

    Part 1: Getting Started with Organic Chemistry . . . . . . . . . . . . . 5CHAPTER 1: The Wonderful World of Organic Chemistry . . . . . . . . . . . . . . . . . . . . . . . . 7CHAPTER 2: DissectingAtoms:AtomicStructureandBonding . . . . . . . . . . . . . . . . . . 15CHAPTER 3: Speaking with Pictures: Drawing Structures . . . . . . . . . . . . . . . . . . . . . . . 35CHAPTER 4: CoveringtheBases(AndtheAcids) . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 57CHAPTER 5: Reactivity Centers: Functional Groups . . . . . . . . . . . . . . . . . . . . . . . . . . . . 67CHAPTER 6: Seeing in 3-D: Stereochemistry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 81

    Part 2: Hydrocarbons . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 97CHAPTER 7: Whats in a Name? Alkane Nomenclature . . . . . . . . . . . . . . . . . . . . . . . . . 99CHAPTER 8: Drawing Alkanes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 107CHAPTER 9: SeeingDouble:TheAlkenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 123CHAPTER 10: Reactions of Alkenes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 137CHAPTER 11:ItTakesAlkynes:TheCarbon-CarbonTripleBond . . . . . . . . . . . . . . . . . 149

    Part 3: Functional Groups . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 157CHAPTER 12:ReplacingandRemoving:SubstitutionandEliminationReactions . . . 159CHAPTER 13: Getting Drunk on Organic Molecules: The Alcohols . . . . . . . . . . . . . . . . 175CHAPTER 14: Side-by-Side: Conjugated Alkenes and the DielsAlder Reaction . . . . . 183CHAPTER 15: Lord of the Rings: Aromatic Compounds . . . . . . . . . . . . . . . . . . . . . . . . . 193CHAPTER 16:BringingOuttheHowitzers:ReactionsofAromaticCompounds . . . . 209

    Part 4: Spectroscopy and Structure Determination . . . . . . . 223CHAPTER 17: A Smashing Time: Mass Spectrometry . . . . . . . . . . . . . . . . . . . . . . . . . . . 225CHAPTER 18:SeeingGoodVibrations:IRSpectroscopy . . . . . . . . . . . . . . . . . . . . . . . . . 241CHAPTER 19:NMRSpectroscopy:HoldontoYourHats,YoureGoingNuclear! . . . . 253CHAPTER 20:FollowingtheClues:SolvingProblemsinNMR . . . . . . . . . . . . . . . . . . . . 273

    Part 5: The Part of Tens . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 293CHAPTER 21:Ten(OrSo)GreatOrganicChemists . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 295CHAPTER 22: Ten Cool Organic Discoveries . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 301CHAPTER 23: Ten Cool Organic Molecules . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 307

  • Part 6: Appendixes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 313APPENDIX A: Working Multistep Synthesis Problems . . . . . . . . . . . . . . . . . . . . . . . . . . 315APPENDIX B: Working Reaction Mechanisms . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 323APPENDIX C: Glossary . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 329

    Index . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 339

  • Table of Contents vii

    Table of ContentsINTRODUCTION . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1

    AboutThisBook . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .2Foolish Assumptions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .3IconsUsedinThisBook . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .3BeyondtheBook . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .4WheretoGofromHere . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .4

    PART 1: GETTING STARTED WITH ORGANIC CHEMISTRY . . . . 5

    CHAPTER 1: The Wonderful World of Organic Chemistry . . . . . . . . . 7ShakingHandswithOrganicChemistry . . . . . . . . . . . . . . . . . . . . . . . . . . . 7WhatAreOrganicMolecules,Exactly? . . . . . . . . . . . . . . . . . . . . . . . . . . . . 9AnOrganicChemistbyAnyOtherName... . . . . . . . . . . . . . . . . . . . . . 11

    Synthetic organic chemists . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .11Bioorganicchemists . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .11Natural products chemists . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .12Physical organic chemists . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .