The complete idiots guide to organic chemistry

Organic
Chemistry
 
by Ian Guch and Kjirsten Wayman, Ph.D.

A member of Penguin Group (USA) Inc.


www.pdfgrip.com


www.pdfgrip.com

Organic
Chemistry


www.pdfgrip.com


www.pdfgrip.com

Organic
Chemistry
 
by Ian Guch and Kjirsten Wayman, Ph.D.

A member of Penguin Group (USA) Inc.


www.pdfgrip.com

For Marcello, who got us started.

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


www.pdfgrip.com

Contents at a Glance
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


www.pdfgrip.com

vi

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


www.pdfgrip.com

Contents at a Glance


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


www.pdfgrip.com


www.pdfgrip.com

 
Contents
Part 1: A Review of General Chemistry


1 Why Study Organic Chemistry?

1
3

What Is Organic Chemistry?.........................................................3
What Is Organic Chemistry Good For?........................................4
Filling the Tank.............................................................................5
Your Plastic Disco Suit...................................................................5

Aspirin: Curing Headaches for Over a Century!............................5
Who Invented Organic Chemistry?...............................................6
Early Chemistry............................................................................6
The Beginnings of Organic Chemistry............................................6
Modern Organic Chemistry...........................................................7
How to Do Well in Organic Chemistry........................................7



2 Covalent Bonding

9

Elementary Atomic Structure...................................................... 10
Chemical Bonding......................................................................... 12
Ionic Bonding: The Jerry Springer Show of Chemistry.................. 13
Covalent Bonding: The Dr. Phil of Chemistry............................ 14
Drawing Lewis Structures........................................................... 15
Polar Bonds................................................................................. 16
Formal Charges........................................................................... 18
Line Drawings............................................................................ 19



3 Pushing Electrons Around

21

Chemistry Is Caused by Moving Electrons................................. 22
What Electrons Want to Do in Neutral Molecules........................ 22

What Electrons Want to Do in Anions......................................... 22
What Electrons Want to Do in Cations........................................ 23
Moving Electrons Around............................................................ 23
The Single-Sided Arrow............................................................... 26
Resonance Structures.................................................................... 27
Drawing Resonance Structures....................................................28



4 What Organic Molecules Look Like

31

An Advertising Interlude.............................................................. 32
sp3 Hybridization........................................................................... 32


www.pdfgrip.com



The Complete Idiot’s Guide to Organic Chemistry
Drawing 3-D Pictures on 2-D Paper........................................... 35
sp2 Hybridization........................................................................... 36
sp Hybridization............................................................................ 37
An Easy Way to Determine the Hybridization of an Atom....... 38



5 Acids and Bases: Our Corrosive Friends

41

Arrhenius Acids and Bases............................................................ 42
Naming the H3O+ Ion................................................................... 42
Brønsted-Lowry Acids and Bases................................................. 43
How to Measure the Strengths of Brønsted-Lowry Acids..............44
Measuring the Strengths of Brønsted-Lowry Bases....................... 47
Factors Affecting Acid Strength................................................... 47
Lewis Acids and Bases...................................................................49

Part 2: Getting Started


6 Alkanes

51
53

What’s an Alkane?........................................................................54
Where Alkanes Come From.........................................................54
Naming Alkanes............................................................................54
Naming Straight Chain Alkanes..................................................54
Alkyl Groups............................................................................... 55
Degrees of Substitution................................................................57
Putting It All Together to Name Alkanes.....................................57
Constitutional Isomerism.............................................................60
Conformations of Alkanes............................................................60
Physical Properties of Alkanes..................................................... 62
Reactions of Alkanes..................................................................... 63

Combustion of Alkanes................................................................. 63
Free Radical Halogenation...........................................................64



7 Cycloalkanes

65

What’s a Cycloalkane?..................................................................66
Naming Cycloalkanes...................................................................66
Cis‑trans Isomerism in Cycloalkanes............................................ 67
Ring Strain....................................................................................69
The Structure of Cyclohexane..................................................... 71
Monosubstituted Cyclohexanes...................................................... 73
Disubstituted Cyclohexanes........................................................... 74


www.pdfgrip.com

Contents


8 Alkenes and Alkynes

77

What Are Alkenes and Alkynes?.................................................. 77
Why Do We Care About Alkenes and Alkynes?........................ 78
Naming Alkenes and Alkynes...................................................... 78

Simple Naming........................................................................... 78
Cis-trans Isomerism in Alkenes....................................................80
E-Z Notation..............................................................................80
Reactions of Alkenes and Alkynes................................................82
Hydrohalogenation Reactions........................................................84
Hydration of Alkenes.................................................................... 85
Halogenations..............................................................................86
Oxidation of Alkenes....................................................................88
The Catalytic Hydrogenation of Alkenes.......................................89



9 Enantiomers, Diastereomers, and Meso, Oh My!

91

What Is Stereochemistry?............................................................92
What Makes a Molecule Chiral?.................................................. 93
Choosing a Name Is Like Clockwork..........................................94
Understanding Diastereomers......................................................96
Examining Meso Compounds......................................................98
Studying Alkene Stereoisomers....................................................99
Step into the Light .......................................................................99
Comparing the Physical and Chemical Properties
of Stereoisomers........................................................................100



10 Let’s Get Substituting!

103

SN2 Reactions.............................................................................. 103
The Mechanism of Sn2 Reactions................................................104
Steric Effects............................................................................. 105
Substrate Restrictions................................................................ 106
Stereochemistry of SN2 Reactions................................................ 107
SN1 Reactions.............................................................................. 107
Steric Effects............................................................................. 109
Substrate Restrictions................................................................ 109
Stereochemistry of SN1 Reactions................................................ 109
So, Which Is It?.......................................................................... 110
Solvent Effects........................................................................... 110
Substrate Effects........................................................................ 111
Nucleophile Effects..................................................................... 112

xi


www.pdfgrip.com

xii

The Complete Idiot’s Guide to Organic Chemistry



11 Elimination Reactions—When Atoms Are Voted Off the Island

113

What Are Elimination Reactions?............................................. 114
E2 Mechanism of Dehydrohalogenation................................... 116
The E1 Mechanism of Dehydrohalogenation............................ 117
Competition Between Elimination and Substitution
Reactions................................................................................... 118
The Strength of the Base/Nucleophile Helps to Determine
the Mechanism........................................................................ 119
The Degree of Substitution in the Substrate Helps to
Determine the Reaction Mechanism......................................... 119
Putting It All Together.............................................................. 122
Anti-Periplanar Elimination Reactions...................................... 124

Part 3: The “Fun” in Functional Groups


12 Haloalkanes: Our Halogenated Friends

127
129

What’s a Haloalkane?................................................................. 130
What Are Haloalkanes Used For?............................................. 130
Naming Haloalkanes.................................................................. 131
Forming Haloalkanes.................................................................. 131
Free-Radical Halogenation......................................................... 132
Hydrohalogenation Reactions...................................................... 134
Halogenation of Alkenes............................................................. 135
Reactions of Haloalkanes............................................................ 135

13 Alcohols: Our Hard‑Partying Friends

137

What Are Alcohols?.................................................................... 138
Naming Alcohols......................................................................... 139
Making Alcohol—It’s Not Just for Moonshiners Anymore!..... 140
Nucleophilic Substitution of Alkyl Halides.................................. 140
Hydration of Alkenes.................................................................. 141
Hydroxylation with OsO4. ......................................................... 141
The Reaction of Carbonyl-Containing Groups with
Organometallic Compounds..................................................... 141
The Reduction of the Carbonyl Group........................................ 142
Reactions of Alcohols.................................................................. 142
Formation of Alkoxides.............................................................. 143
Acid‑Catalyzed Dehydration...................................................... 143


www.pdfgrip.com

Contents
Substitution of Alcohols with Hydrogen Halides to Form
Haloalkanes............................................................................. 146
The Oxidation of Alcohols.......................................................... 147



14 The Intoxicating Smell of Ethers

149

What Are Ethers?....................................................................... 150
What Are Ethers Good For?...................................................... 150
How to Name Ethers.................................................................. 150
IUPAC Naming of Ethers......................................................... 150
Common Names........................................................................ 151
The Names People Actually Use................................................. 151
Physical Properties of Ethers...................................................... 152
The Formation of Ethers............................................................ 152
Williamson Ether Synthesis....................................................... 152
Dehydration of Alcohols.............................................................. 153
Formation of Epoxides............................................................... 154
Reactions of Ethers..................................................................... 154
Autoxidation of Ethers............................................................... 154
Ring-Opening Reactions of Epoxides.......................................... 155



15 The Sweet Bouquet of Aromatic Compounds

159

What Are Aromatic Molecules?................................................. 160
Naming Aromatic Compounds.................................................. 160
Monosubstituted Benzenes.......................................................... 161
Disubstituted Benzenes.............................................................. 161
Even More Substituted Benzene Derivatives.............................. 162
When Benzene Is the Substituent............................................... 163

Molecules with More Than One Aromatic Ring......................... 163
Electrophilic Aromatic Substitution.......................................... 164
The General Mechanism of Electrophilic Aromatic
Substitutions............................................................................ 164
Bromination and Chlorination................................................... 165
Nitration................................................................................... 166
Sulfonation................................................................................ 166
Friedel-Crafts Alkylation........................................................... 166
Friedel-Crafts Acylations........................................................... 167
Substituent Effects in Electrophilic Aromatic Substitutions.... 167
Ortho-/Para- Directing and Activating Groups........................ 167
Meta- Directing and Deactivating Groups................................. 169

xiii


www.pdfgrip.com

xiv

The Complete Idiot’s Guide to Organic Chemistry
Ortho-/Para- Directing and Deactivating Groups..................... 171
More Than One Substituent...................................................... 172



16 Amines—the Smell of Victory!

175

What Are Amines?...................................................................... 176
Some General Classes of Amines................................................ 176
Naming Amines.......................................................................... 177
IUPAC Naming........................................................................ 178
Common Names........................................................................ 179
The Properties of Amines.......................................................... 180
Hydrogen Bonding in Amines.................................................... 180
Acidity and Basicity in Amines................................................... 181
The Synthesis of Amines............................................................ 182
Alkylation of Ammonia and Amines.......................................... 182
Gabriel Synthesis of Amines....................................................... 183
Reduction of Nitrobenzene......................................................... 183
Reductive Animations................................................................ 184
Common Reactions of Amines................................................... 184
The Formation of Diazonium Salts............................................ 184
The Reaction of Aryldiazonium Salts with
Hypophosphorous Acid.............................................................. 185
The Decomposition of Aryldiazonium Salts................................ 186



17 All About Aldehydes and Ketones

189

What Are Aldehydes and Ketones?............................................ 190
Naming Aldehydes and Ketones................................................ 190
Common Naming...................................................................... 191
IUPAC Naming........................................................................ 192
Properties of Aldehydes and Ketones......................................... 193

Synthesis of Aldehydes and Ketones.......................................... 194
Friedel-Crafts Acylation............................................................ 194
Oxidation of 1° Alcohols to Make Aldehydes............................... 195
Oxidation of 2° Alcohols to Make Ketones.................................. 195
Reactions of Aldehydes and Ketones.......................................... 196
Reaction with Grignard Reagents.............................................. 196
Reducing Carbonyls to Alkanes................................................. 198
The Clemmensen Reduction....................................................... 198
Wolff-Kishner Reduction............................................................ 199


www.pdfgrip.com

Contents
The Formation of Acetals........................................................... 199
Formation of Imines and Enamines............................................ 201
Reductive Amination of Carbonyls..............................................202
Reduction of Carbonyls to Alcohols..............................................202
Keto/Enol Tautomerism.............................................................203



18 Carboxylic Acids

207

What’s a Carboxylic Acid?.......................................................... 207
Naming Carboxylic Acids...........................................................208
Common Names for Carboxylic Acids.........................................208
IUPAC Names for Carboxylic Acids...........................................209

Properties of Carboxylic Acids................................................... 210
How to Make Carboxylic Acids.................................................. 211
Reactions of Carboxylic Acids.................................................... 211
Reducing Carboxylic Acids......................................................... 212
Fischer Esterification................................................................. 213
Conversion of Carboxylic Acids to Acid Halides........................... 215
Decarboxylation Reactions.......................................................... 215



19 Carboxylic Acid Derivatives

219

Getting to Know the Carboxylic Acid Derivatives................... 219
Acid Halides.............................................................................. 220
Acid Anhydrides........................................................................ 220
Esters........................................................................................ 220
Amides...................................................................................... 221
Nucleophilic Acyl Substitution................................................... 222
Reactions of Carboxylic Acid Derivatives.................................. 223
Hydrolysis Reactions................................................................... 224
Esterification Reactions.............................................................. 225
Formation of Amides................................................................. 226
Grignard Addition to Esters...................................................... 226
Reduction Reactions................................................................... 228



20 The Return of the Enolate

231

Reviewing Keto/Enol Tautomerization..................................... 232
The Acidity of α‑Carbon Atoms................................................ 233
Enolates Are Nucleophiles!......................................................... 234
The Aldol Reaction..................................................................... 235
Crossed Aldol Reactions.............................................................. 236
Dehydration of β‑Hydroxyaldehydes........................................... 237

xv


www.pdfgrip.com

xvi

The Complete Idiot’s Guide to Organic Chemistry
Aldol-Related Reactions.............................................................. 238
Aldol Reactions with Ketones...................................................... 238
Claisen Condensations................................................................ 239
Other Reactions That Involve Fun with Enolates..................... 241
α,β-Unsaturated Carbonyls....................................................... 241

Part 4: Spectacular Spectroscopy


21 Introducing the Magical World of Spectroscopy

245

247

What Is Spectroscopy?............................................................... 248
Wavelength, Frequency, and the Speed O’ Light...................... 248
Light and Energy........................................................................ 249
Colors and Energy...................................................................... 250
What Happens When You Add Electromagnetic Radiation
to Something?........................................................................... 252
Types of Spectroscopy Used in Organic Chemistry................. 253
Why Spectroscopy Is Useful...................................................... 254



22 Hot on the Trail of Infrared Spectroscopy

257

What Is Infrared Radiation?...................................................... 258
What Are We Measuring, Anyway?.......................................... 258
What’s in an IR Spectrometer?.................................................. 259
Introduction to IR Spectra.........................................................260
IR Spectra by Functional Group............................................... 261
Alkanes..................................................................................... 261
Alkenes...................................................................................... 261
Alkynes...................................................................................... 262
Aromatic Compounds................................................................. 263
Alcohols.....................................................................................264
Amines......................................................................................264
Ethers........................................................................................ 265
Carbonyl‑Containing Compounds............................................... 265

A Handy Chart to Make Your Life Easier................................. 268
Figuring Out What You’ve Got................................................. 269



23 NMR—You’ll (Spin) Flip Your Lid!

275

What the Heck Is NMR?........................................................... 275
What Makes the Nuclei Different from One Another?...............277
What Does an NMR Spectrum Look Like?................................ 278


www.pdfgrip.com

Contents xvii
Interpreting 1H‑NMR Spectra...................................................280
Carbon‑13 NMR.........................................................................284
What a 13C NMR Spectrum Looks Like.................................... 286
13
C NMR Chemical Shifts.........................................................287

Part 5: Very Basic Biochemistry


24 Carbohydrates: How Sweet It Is!

289
291

What Are Carbohydrates?.......................................................... 292
Monosaccharides......................................................................... 293
Stereochemistry of Monosaccharides............................................ 294
Monosaccharides Get Cyclic........................................................ 295
Disaccharides...............................................................................298
Polysaccharides............................................................................300



25 Amino Acids and Proteins: The Legos of Biochemistry

303

You Already Know What an Amino Acid Is.............................304
Meet the Amino Acids................................................................304
“Need to Knows” About the Common Amino Acids.....................307
Don’t Really “Need to Knows” About the Common
Amino Acids............................................................................308
Zwitterion!...................................................................................308
Peptides and Protein...................................................................309
Naming Peptides and Proteins................................................... 311
Protein Structures....................................................................... 312
Primary (1°) Structure............................................................. 312
Secondary (2°) Structure........................................................... 313
Tertiary (3°) Structure.............................................................. 314
Quaternary (4°) Structures....................................................... 315

Appendixes

A Glossary

317



B Solutions to “You’ve Got Problems”

331

  Index

343


www.pdfgrip.com


www.pdfgrip.com

Introduction
Organic chemistry is scary. When you sign up for the class, lots of people tell you
that it was the hardest class that they ever took and that it’s impossible to do well. The
first day of class, the professor goes up to the front of the room and draws lots of little diagrams that he says are molecules but just look like really neat geometric shapes.
The words your professor uses sound like they mean something, but they are hard to
translate into English.
The problem with this description is that organic chemistry doesn’t need to be scary.
Though organic chemistry seems a lot different from your general chemistry class,
the concepts are exactly the same except that they are applied to molecules that contain carbon. As for your friends who told you that organic chemistry is the hardest

class ever, keep in mind that the people who complain loudest are usually in the
minority. Think of all the people who take organic chemistry who aren’t complaining!
Now, just because organic chemistry isn’t as bad as you’ve been led to believe doesn’t
mean that you can just coast by and collect an excellent grade. Like any chemistry
class, you’re going to have to spend some time studying and trying to figure out what
all of this means. Fortunately, you’ve bought this book (which is pretty good, if I do
say so myself), which should help you to get through the rough patches.
Though it may be immodest to say so, the authors of this book are also exactly the
right people to help you learn chemistry. I (your main narrarator Ian) am a high
school chemistry teacher who is used to explaining scary concepts in easy-tounderstand terms. My coauthor (Kjirsten) is a college organic chemistry professor
who teaches this stuff all the time and knows exactly what your teacher thinks is
important. Between the two of us and all that prior chemistry knowledge floating
around in your brain, you can’t help but become an organic chemistry pro!
The bottom line is this: Relax! You can and will learn organic chemistry!

How This Book Is Organized
We’ve conveniently broken up this book into a few sections:
Part 1, “A Review of General Chemistry,” is meant to refresh your memory about
some of the most important topics from general chemistry that come up in most
organic chemistry classes. Even if you scored 100 percent on every test you took
in general chemistry, it might not be a bad idea to review this part, just in case you
forgot something.


www.pdfgrip.com

xx

The Complete Idiot’s Guide to Organic Chemistry
Part 2, “Getting Started,” is an introduction to some of the simplest ideas in

organic chemistry. In this part, you’ll learn about the simple organic compounds that
provide the basis for the complicated ones you’ll see later. You’ll also get to meet the
two most important types of organic reactions that you’ll need to know.
In Part 3, “The ‘Fun’ in Functional Groups,” you’ll learn about the most
commonly found functional groups that are used in organic chemistry. From alcohols
to carboxylic acids to other compounds you’ve never even heard of before, you’ll learn
it all.
If you’ve ever wondered how people are able to figure out what chemical compounds
are present in those little flasks, Part 4, “Spectacular Spectroscopy,” will answer
these questions. For those of you who like acronyms, here are two fun ones: NMR
and IR!
Finally, we’ll wrap up the book with a discussion of very basic biochemistry. Because
biochemistry is such a complex topic (which is why there are separate classes in
it), we’ve decided to call this part, straightforwardly enough, Part 5, “Very Basic
Biochemistry.”

Special Features and Random Thoughts
Occasionally, I feel the need to share some little tidbit of knowledge with you.
Depending on the content of this little tidbit, I will put it in one of the following
sidebars:

Bad Reactions

The Mole Says
Ideas that you absolutely,
positively need to know.

Common mistakes that you
should avoid at all costs.

Chemistrivia
Definitions of complicated words
and ideas.

Information that may not help
you on the test, but may come
in handy at a cocktail party.

You’ve Got Problems
Practice problems that help you better understand the material covered in each section.


www.pdfgrip.com

Introduction

xxi

Acknowledgements
No book is written without the help of a bunch of people who don’t get their names
on the cover (and usually don’t get paid, either). Though we didn’t feel grateful
enough to send them a check, we do want to take the opportunity to thank them for
their invaluable help.
Both Ian and Kjirsten want to thank the following:
Marcello DiMare, for getting both of us started on our path in organic chemistry.
Without his patient help and inspiration, we might have become physical chemists,
dooming us to a life of differential equations. Thanks, Marcello!
Jessica Faust at BookEnds for getting us this book deal, and Mike Sanders at Alpha/
Penguin for putting up with our nonsense. Although we like to give Mike a hard
time (and he seems to like giving us a hard time, too), we’re very grateful for his help

and guidance. We also want to thank the other folks at Alpha/Penguin who worked
behind the scenes to make this book work so well.
Our young proofreaders: Sara Rainey, Mingyu Kim, Andrew Dailey, Brittney Lala,
Hunter Bohlen, and Erica Tangney. Thanks for reading this thing over during your
summer vacation so that we wouldn’t have to answer for our dangling participles to
the many readers of this book!
And, special thanks to you, the readers, without whom we would not have had the
excuse or excitement for writing this book
Ian Guch wants to thank the following folks: To Ingrid, my wife, thanks for making
my life sunny and sweet. Melina, thanks for being such an awesome kid! To my
parents, brother, grandparents, and rest of my family, thanks for all of your support
through the years. I also want to thank my friends (you degenerates), everybody I’ve
been in a band with over the years (you degenerates), Monsignor Raymond East and
my family at St. Teresa of Avila Catholic Church for all their support, and God, to
whom all glory and honor are due. Most of all, I want to thank my co-author Kjirsten,
who is responsible for all of the good parts of the book. (The mistakes are mine.)
Kjirsten Wayman wants to thank the following: To my parents, family, and friends
(who are like my family) for all their love and support in getting me to where I am
today. Thanks to Tarek Sammakia, my Ph.D. advisor, for giving me the skills to
understand organic chemistry and being a good role model to teach it. Thanks to my
supportive colleagues, and especially Joshua Smith for random consultations regarding this book. Thanks to Humboldt State University for granting me a sabbatical
so I could travel to New Zealand and research the organic compounds from native
plant extracts. Thanks to the short daylight hours and the endless wind and cold of


www.pdfgrip.com

xxii The Complete Idiot’s Guide to Organic Chemistry
Dunedin, New Zealand, winters for the inspiration to stay inside and work on this
book. Above all, I want to thank my coauthor Ian, without whose narrative talents

and questionable humor this book would not be nearly so exciting.

Trademarks
All terms mentioned in this book that are known to be or are suspected of being
trademarks or service marks have been appropriately capitalized. Alpha Books and
Penguin Group (USA) Inc. cannot attest to the accuracy of this information. Use of
a term in this book should not be regarded as affecting the validity of any trademark
or service mark.


www.pdfgrip.com

1

Part

A Review of General
Chemistry

Welcome to organic chemistry! You’re probably thinking that we’re going
to throw a bunch of scary diagrams and formulas at you in the next couple
of pages.
Relax! Before we give you all the organic stuff, we want to make sure that
you’re comfortable with all of the general chemistry that you (hopefully)
learned before taking on the challenge of organic chemistry. If you’re
a general chemistry pro, the next few chapters should be an easy stroll
through the woods. For those of you who may have had trouble in general
chemistry, don’t worry, we’ll make sure that you learn everything you need.