Organic Chemistry I For Dummies

405 Pages·2014·10.45 MB·English

by  Arthur Winter

Science/Chemistry/Organic
Making Everything Easier!™ 2nd Edition
2nd Edition
The fun and easy way O rg a n i c
Open the book and find: O
to take the confusion
r
out of organic chemistry • Tips on deciphering
g
“organic speak” a m i s t r y I
If you’re feeling challenged by organic chemistry, fear not! • How to determine the C h e
n
This easy-to-understand guide explains the basic principles structure of a molecule
in simple terms, providing insight into the language of i
• A complete overview of c
organic chemists, the major classes of compounds, and more. chemical reactions
C
Complete with new explanations and example equations, this
• Strategies for solving organic
book will help you ace your organic chemistry class! h
chemistry problems
e
• Go organic — get an introduction to organic chemistry, • Tricks to prepare for organic
m
from dissecting atoms and the basics of bases and acids, chemistry exams
to stereochemistry and drawing structures
• Renewed example equations i
• Hydrocarbons — dive into hydrocarbons, including a full in this new edition s
explanation of alkanes, alkenes, and alkynes t
• New explanations and r
• Functional groups — understand substitution and elimination
practical examples y
reactions, the alcohols, conjugated alkenes, aromatic

compounds, and much more I
• 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
• Grasp the principles of organic
chemistry class, along with information on cool organic
chemistry at your own pace
discoveries, and ten of the greatest organic chemists
• Score your highest in your
Go to Dummies.com®
Arthur Winter is a graduate of Frostburg State University, where he 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 781118828076 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.
Check out our
• Videos
• Illustrated Articles
• Step-by-Step Instructions
Plus, each month you can win valuable prizes by entering
our Dummies.com sweepstakes. *
Want a weekly dose of Dummies? Sign up for Newsletters on
• Digital Photography
• Microsoft Windows & Office
• Personal Finance & Investing
• Health & Wellness
• Computing, iPods & Cell Phones
• eBay
• Internet
• Food, Home & Garden
Find out “HOW” at Dummies.com
*Sweepstakes not currently available in all countries; visit Dummies.com for official rules.
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, [phone],
fax [phone], 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 [phone]. 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
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
viii
Organic Chemistry I For Dummies, 2nd Edition
Chapter 3: Speaking with Pictures: Drawing Structures . . . . . . . . . . . 35
Picture-Talk: Lewis Structures .....................................................................37
Taking charge: Assigning formal charges .........................................37
Drawing structures ..............................................................................39
Atom packing: Condensed structures ...............................................40
Structural shorthand: Line-bond structures ....................................41
Converting Lewis structures to line-bond structures .....................41
Determining the number of hydrogens on 
line-bond structures ........................................................................43
So lonely: Determining lone pairs on atoms .....................................44
Problem Solving: Arrow Pushing .................................................................45
Drawing Resonance Structures ....................................................................47
Rules for resonance structures ..........................................................48
Problem solving: Drawing resonance structures.............................49
Drawing more than two resonance structures ................................53
Assigning importance to resonance structures ...............................54
Common mistakes in drawing resonance structures ......................56
Chapter 4: Covering the Bases (And the Acids) . . . . . . . . . . . . . . . . . . . 59
A Defining Moment: Acid-Base Definitions .................................................60
Arrhenius acids and bases: A little watery .......................................60
Pulling for protons: Brønsted-Lowry acids and bases ....................61
Electron lovers and haters: Lewis acids and bases .........................62
Comparing Acidities of Organic Molecules ................................................63
Comparing atoms .................................................................................64
Seeing atom hybridization ..................................................................65
Seeing electronegativity effects .........................................................65
Seeing resonance effects .....................................................................66
Defining pKa: A Quantitative Scale of Acidity ............................................67
Problem Solving: Predicting the Direction of Acid-Base Reactions
at Equilibrium .............................................................................................68
Chapter 5: Reactivit y Centers: Functional Groups . . . . . . . . . . . . . . . . 69
Hydrocarbons ................................................................................................70
Double the fun: The alkenes ...............................................................70
Alkynes of fun .......................................................................................72
Smelly compounds: The aromatics ...................................................73
Singly Bonded Heteroatoms .........................................................................74
Happy halides .......................................................................................74
For rubbing and drinking: Alcohols ...................................................76
What stinks? Thiols .............................................................................76
How ethereal ........................................................................................77
Carbonyl Compounds ...................................................................................78
Living on the edge: Aldehydes ...........................................................78
Stuck in the middle: Ketones ..............................................................79