Chemistry by Ian Guch and Kjirsten Wayman, Ph.D. A member of Penguin Group (USA) Inc.
Chemistry
Chemistry by Ian Guch and Kjirsten Wayman, Ph.D. A member of Penguin Group (USA) Inc.
ALPHA BOOKS Published by the Penguin Group Penguin Group (USA) Inc., 375 Hudson Street, New York, New York 10014, USA Penguin Group (Canada), 90 Eglinton Avenue East, Suite 700, Toronto, Ontario M4P 2Y3, Canada (a division of Pearson Penguin Canada Inc.) Penguin Books Ltd., 80 Strand, London WC2R 0RL, England Penguin Ireland, 25 St. Stephen’s Green, Dublin 2, Ireland (a division of Penguin Books Ltd.) Penguin Group (Australia), 250 Camberwell Road, Camberwell, Victoria 3124, Australia (a division of Pearson Australia Group Pty. Ltd.) Penguin Books India Pvt. Ltd., 11 Community Centre, Panchsheel Park, New Delhi—110 017, India Penguin Group (NZ), 67 Apollo Drive, Rosedale, North Shore, Auckland 1311, New Zealand (a division of Pearson New Zealand Ltd.) Penguin Books (South Africa) (Pty.) Ltd., 24 Sturdee Avenue, Rosebank, Johannesburg 2196, South Africa Penguin Books Ltd., Registered Offices: 80 Strand, London WC2R 0RL, England Copyright © 2007 by Ian Guch and Kjirsten Wayman, Ph.D. All rights reserved. No part of this book shall be reproduced, stored in a retrieval system, or transmitted by any means, electronic, mechanical, photocopying, recording, or otherwise, without written permission from the publisher. No patent liability is assumed with respect to the use of the information contained herein. Although every precaution has been taken in the preparation of this book, the publisher and authors assume no responsibility for errors or omissions. Neither is any liability assumed for damages resulting from the use of information contained herein. For information, address Alpha Books, 800 East 96th Street, Indianapolis, IN 46240. THE COMPLETE IDIOT’S GUIDE TO and Design are registered trademarks of Penguin Group (USA) Inc. I S BN: 1-4362-4303-3 Library of Congress Catalog Card Number: 2007941345 Note: This publication contains the opinions and ideas of its authors. It is intended to provide helpful and informative material on the subject matter covered. It is sold with the understanding that the authors and publisher are not engaged in rendering professional services in the book. If the reader requires personal assistance or advice, a competent professional should be consulted. The authors and publisher specifically disclaim any responsibility for any liability, loss, or risk, personal or otherwise, which is incurred as a consequence, directly or indirectly, of the use and application of any of the contents of this book. Publisher: Marie Butler-Knight Editorial Director/Acquiring Editor: Mike Sanders Senior Managing Editor: Billy Fields Development Editor: Nancy D. Lewis Production Editor: Kayla Dugger Copy Editor: Cate Schwenk Cartoonist: Steve Barr Book Designer: Trina Wurst Indexer: Brad Herriman Layout: Brian Massey Proofreaders: Megan Wade, Mary Hunt
Part 1: A Review of General Chemistry 1 1 Why Study Organic Chemistry? A brief overview of organic chemistry and some of the people who brought it to you. 3 2 Covalent Bonding The story of the covalent bond and how to represent it. 9 3 Pushing Electrons Around Your handy guide to understanding how to draw the many arrows that are common in organic chemistry. 21 4 What Organic Molecules Look Like The joys of hybridization, plus a commercial break from the makers of every molecular model kit. 31 5 Acids and Bases: Our Corrosive Friends Eat away at your fears of organic chemistry with this review of our little corrosive friends. 41 Part 2: Getting Started 51 6 Alkanes This is where the organic excitement begins. Fortunately, it’s not where it ends! 53 7 Cycloalkanes If the alkanes are considered the parents of organic chemistry, think of the cycloalkanes as organic chemistry’s wacky aunt and uncle. 65 8 Alkenes and Alkynes Everything you ever wanted to know (and lots of things you probably didn’t) about multiple bonding but were afraid to ask. 77 9 Enantiomers, Diastereomers, and Meso, Oh My! Get out the molecular models and learn all about stereochemistry. 91 10 Let’s Get Substituting! Substitution reactions make up a lot of organic chemistry. Fortunately, we’ve packaged the important stuff in this chapter. 103
The Complete Idiot’s Guide to Organic Chemistry 11 Elimination Reactions—When Atoms Are Voted Off the Island Learn how to get those pesky functional groups off of organic compounds through the miracle of elimination reactions. Part 3: The “Fun” in Functional Groups 113 127 12 Haloalkanes: Our Halogenated Friends What happens when you put an alkane and halogen atoms in the same molecule? Find out here! 129 13 Alcohols: Our Hard-Partying Friends Find out what else alcohol is good for! 137 14 The Intoxicating Smell of Ethers The story of how ethers can be used for either good (via chemistry) or evil (via inhalation). 149 15 The Sweet Bouquet of Aromatic Compounds Okay … these compounds may not smell all that great, but they sure are good in organic synthesis. Find out more about them here! 159 16 Amines—The Smell of Victory! Though amines smell like rotten fish (at best), they come in handy for a variety of organic reactions. 175 17 All About Aldehydes and Ketones Our introduction into the world of the carbonyl group. 189 18 Carboxylic Acids The care, feeding, and reactions of molecules with the –CO2H group. 207 19 Carboxylic Acid Derivatives The little brothers and sisters of the carboxylic acids come out to play. Amides, esters, acid anhydrides, and acid halides as you’ve never seen them before! 219 20 The Return of the Enolate How enolates make a wide variety of organic reactions possible. 231 Part 4: Spectacular Spectroscopy 21 Introducing the Magical World of Spectroscopy Learn the basics of spectroscopy and find out what it’s good for. 245 247
22 Hot on the Trail of Infrared Spectroscopy How to make and (more importantly) interpret infrared spectra. 257 23 NMR—You’ll (Spin) Flip Your Lid! Have you ever wondered how a nuclear magnetic resonance spectrometer works? If you have (and even if you haven’t), your questions will be answered here! 275 Part 5: Very Basic Biochemistry 24 Carbohydrates: How Sweet It Is! Though they’re sometimes maligned by dieters, we’ll find out what carbohydrates are and learn about some of their fascinating and disgusting uses. 25 Amino Acids and Proteins: The Legos of Biochemistry The story of amino acids and how you can make them into big proteins. 289 291 303 Appendixes A Glossary 317 B Solutions to “You’ve Got Problems” 331 Index 343 vii
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