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- Herausgeber: John Wiley & Sons
- Kategorie: Wissenschaft und neue Technologien
- Sprache: Englisch
- Veröffentlichungsjahr: 2021
Need help with organic chemistry? Get extra practice with this workbook If you're looking for a little extra help with organic chemistry than your Organic Chemistry I class offers, Organic Chemistry I Workbook For Dummies is exactly what you need! It lets you take the theories you're learning (and maybe struggling with) in class and practice them in the same format you'll find on class exams and other licensing exams, like the MCAT. It offers tips and tricks to memorize difficult concepts and shortcuts to solving problems. This reference guide and practice book explains the concepts of organic chemistry (such as functional groups, resonance, alkanes, and stereochemistry) in a concise, easy-to-understand format that helps you refine your skills. It also includes real practice with hundreds of exam questions to test your knowledge. * Walk through the answers and clearly identify where you went wrong (or right) with each problem * Get practical advice on acing your exams * Use organic chemistry in practical applications Organic Chemistry I Workbook For Dummies provides you with opportunities to review the material and practice solving problems based on the topics covered in a typical Organic Chemistry I course. With the help of this practical reference, you can face down your exam and pass on to Organic Chemistry II with confidence!
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Organic Chemistry I Workbook For Dummies,® 2nd Edition
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Library of Congress Control Number: 2021950191
ISBN 978-1-119-85577-4 (pbk); ISBN 978-1-119-85578-1 (ebk); ISBN 978-1-119-85579-8 (ebk)
Organic Chemistry I Workbook For Dummies®
To view this book's Cheat Sheet, simply go to www.dummies.com and search for “Organic Chemistry I Workbook For Dummies Cheat Sheet” in the Search box.
Table of Contents
Cover
Title Page
Copyright
Introduction
About This Book
Foolish Assumptions
Icons Used in This Book
Beyond the Book
Where to Go from Here
Part 1: The Fundamentals of Organic Chemistry
Chapter 1: Working with Models and Molecules
Constructing Lewis Structures
Predicting Bond Types
Determining Bond Dipoles
Determining Dipole Moments for Molecules
Predicting Atom Hybridizations and Geometries
Making Orbital Diagrams
Answer Key
Chapter 2: Speaking Organic Chemistry: Drawing and Abbreviating Lewis Structures
Assigning Formal Charges
Determining Lone Pairs on Atoms
Abbreviating Lewis Structures with Condensed Structures
Drawing Line-Bond Structures
Determining Hydrogens on Line-Bond Structures
Answer Key
Chapter 3: Drawing Resonance Structures
Seeing Cations Next to a Double Bond, Triple Bond, or Lone Pair
Pushing Lone Pairs Next to a Double or Triple Bond
Pushing Double or Triple Bonds Containing an Electronegative Atom
Alternating Double Bonds around a Ring
Drawing Multiple Resonance Structures
Assigning Importance to Resonance Structures
Answer Key
Chapter 4: Working with Acids and Bases
Defining Acids and Bases
Comparing Acidities of Organic Molecules
Predicting Acid-Base Equilibria Using pKa Values
Answer Key
Part 2: The Bones of Organic Molecules: The Hydrocarbons
Chapter 5: Seeing Molecules in 3-D: Stereochemistry
Identifying Chiral Centers and Assigning Substituent Priorities
Assigning R & S Configurations to Chiral Centers
Working with Fischer Projections
Comparing Relationships between Stereoisomers and Meso Compounds
Answer Key
Chapter 6: The Skeletons of Organic Molecules: The Alkanes
Understanding How to Name Alkanes
Drawing a Structure from a Name
Answer Key
Chapter 7: Shaping Up with Bond Calisthenics and Conformation
Setting Your Sights on Newman Projections
Comparing Conformational Stability
Choosing Sides: The Cis-Trans Stereochemistry of Cycloalkanes
Getting a Ringside Seat with Cyclohexane Chair Conformations
Predicting Cyclohexane Chair Stabilities
Answer Key
Chapter 8: Doubling Down: The Alkenes
Giving Alkenes a Good Name
Markovnikov Mixers: Adding Hydrohalic Acids to Alkenes
Adding Halogens and Hydrogen to Alkenes
Just Add Water: Adding H
2
O to Alkenes
Seeing Carbocation Rearrangements
Answer Key
Chapter 9: Tripling the Fun: Alkyne Reactions and Nomenclature
Playing the Name Game with Alkynes
Adding Hydrogen and Reducing Alkynes
Adding Halogens and Hydrohalic Acids to Alkynes
Adding Water to Alkynes
Creating Alkynes
Back to the Beginning: Working Multistep Synthesis Problems
Answer Key
Part 3: Functional Groups and Their Reactions
Chapter 10: The Leaving Group Boogie: Substitution and Elimination of Alkyl Halides
The Replacements: Comparing S
N
1 and S
N
2 Reactions
Kicking Out Leaving Groups with Elimination Reactions
Putting It All Together: Substitution and Elimination
Answer Key
Chapter 11: Not as Thunk as You Drink I Am: The Alcohols
Name Your Poison: Alcohol Nomenclature
Beyond Homebrew: Making Alcohols
Transforming Alcohols (without Committing a Party Foul)
Answer Key
Chapter 12: Conjugated Dienes and the Diels-Alder Reaction
Seeing 1,2- and 1,4-Addition Reactions to Conjugated Dienes
Dienes and Their Lovers: Working Forward in the Diels-Alder Reaction
Reverse Engineering: Working Backward in the Diels-Alder Reaction
Answer Key
Chapter 13: The Power of the Ring: Aromatic Compounds
Determining Aromaticity, Anti-aromaticity, or Nonaromaticity of Rings
Figuring Out a Ring System’s MO Diagram
Dealing with Directors: Reactions of Aromatic Compounds
Order! Tackling Multistep Synthesis of Poysubstituted Aromatic Compounds
Answer Key
Part 4: Detective Work: Spectroscopy and Spectrometry
Chapter 14: Breaking Up (Isn’t Hard to Do): Mass Spectrometry
Identifying Fragments in the Mass Spectrum
Predicting a Structure Given a Mass Spectrum
Answer Key
Chapter 15: Cool Vibrations: IR Spectroscopy
Distinguishing between Molecules Using IR Spectroscopy
Identifying Functional Groups from an IR Spectrum
Answer Key
Chapter 16: Putting Molecules under the Magnet: NMR Spectroscopy
Seeing Molecular Symmetry
Working with Chemical Shifts, Integration, and Coupling
Putting It All Together: Solving for Unknown Structures Using Spectroscopy
Answer Key
Part 5: The Part of Tens
Chapter 17: The Ten Commandments of Organic Chemistry
Thou Shalt Work the Practice Problems before Reading the Answers
Thou Shalt Memorize Only What Thou Must
Thou Shalt Understand Thy Mechanisms
Thou Shalt Sleep at Night and Not in Class
Thou Shalt Read Ahead Before Class
Thou Shalt Not Fall Behind
Thou Shalt Know How Thou Learnest Best
Thou Shalt Not Skip Class
Thou Shalt Ask Questions
Thou Shalt Keep a Positive Outlook
Chapter 18: Ten Tips for Acing Orgo Exams
Scan and Answer the Easy Questions First
Read All of Every Question
Set Aside Time Each Day to Study
Form a Study Group
Get Old Exams
Make Your Answers Clear by Using Structures
Don’t Try to Memorize Your Way Through
Work a Lot of Problems
Get Some Sleep the Night Before
Recognize Red Herrings
Chapter 19: Ten Cool Natural Products
Maitotoxin
Penicillin
Nicotine
THC
Morphine
Taxol
Bombykol
The Green Fluorescent Protein Fluorophore
Ladderanes
Caffeine
Index
About the Author
Advertisement Page
Connect with Dummies
End User License Agreement
List of Tables
Chapter 1
Table 1-1 The Hybridization of an Atom
Chapter 6
Table 6-1 Parent and Substituent Names
Chapter 8
Table 8-1 Naming the Parent Chains
Chapter 10
Table 10-1 Structural Preferences for Replacements
Table 10-2 Reaction Conditions for Elimination Mechanisms
Chapter 15
Table 15-1 IR Absorption of Common Functional Groups
Chapter 16
Table 16-1 Common Fragments
List of Illustrations
Chapter 1
FIGURE 1-1: Electronegativity values for common atoms.
Chapter 2
FIGURE 2-1: Charge patterns for common atoms.
Chapter 4
FIGURE 4-1: Bronsted-Lowry acids and bases reacting.
FIGURE 4-2: Lewis acids and bases.
Chapter 5
FIGURE 5-1: Breaking ties when prioritizing substituents.
FIGURE 5-2: Double and triple bonds using the Cahn-Ingold-Prelog rules.
FIGURE 5-3: Using wedges and dashes.
FIGURE 5-4: Converting a 3-D representation to a Fischer projection.
Chapter 6
FIGURE 6-1: Common names for complex substituents.
Chapter 7
FIGURE 7-1: Newman projection of ethane.
FIGURE 7-2: Building the Newman projection of ethane.
FIGURE 7-3: Eclipsed and staggered conformations.
FIGURE 7-4: Anti, gauche, eclipsed, and totally eclipsed conformations.
FIGURE 7-5:
Cis
and
trans
configurations.
FIGURE 7-6: A chair cyclohexane with axial and equatorial hydrogens.
FIGURE 7-7: Performing a chair ring flip.
Chapter 8
FIGURE 8-1: Mechanism of hydrohalic addition to alkenes.
FIGURE 8-2: H
2
and
X
2
addition reactions to alkenes.
FIGURE 8-3: Markovnikov addition of water to an alkene via the oxymercuration/d...
FIGURE 8-4: Anti-Markovnikov addition of water to an alkene via the hydroborati...
FIGURE 8-5: Hydride and alkyl shifts.
FIGURE 8-6: A carbocation ring expansion of a five-membered ring.
Chapter 9
FIGURE 9-1: Halogen-ation and hydrohalic acid addition reactions of alkynes.
FIGURE 9-2: Markovnikov and anti-Markovnikov addition of water to alkynes.
FIGURE 9-3: Making alkynes by double dehydrohalogenation.
FIGURE 9-4: Making alkynes using acetylide chemistry.
Chapter 10
FIGURE 10-1: The mechanisms of the S
N
1 and S
N
2 reactions, in which a nucleophil...
FIGURE 10-2: The mechanisms of the E1 and E2 reactions, in which a base (B:
–
...
FIGURE 10-3: A reaction tree for distinguishing among the four substitution and...
Chapter 11
FIGURE 11-1: Making alcohols by reduction reactions.
FIGURE 11-2: Grignard reactions.
FIGURE 11-3: Comparing PCC and Jones’ oxidations of primary alcohols.
FIGURE 11-4: The Williamson ether synthesis.
Chapter 12
FIGURE 12-1: The 1,2- and 1,4-addition reactions of a hydrogen halide (H-
X
) to ...
FIGURE 12-2: Reaction coordinate diagram showing kinetic and thermodynamic prod...
FIGURE 12-3: The Diels-Alder reaction.
FIGURE 12-4: Dienes in rings lead to bicyclic products.
Chapter 13
FIGURE 13-1: The three possible orientations of a disubstituted benzene.
FIGURE 13-2: Reagents for preparing substituted benzenes.
FIGURE 13-3: Three additional aromatic reactions you should know.
Chapter 14
FIGURE 14-1: How molecules break apart in a mass spectrometer.
FIGURE 14-2: The McLafferty rearrangement.
Guide
Cover
Title Page
Copyright
Table of Contents
Begin Reading
Index
About the Author
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Introduction
Organic chemistry is a subject that blends basic chemistry, logic problems, 3-D puzzles, and stick-figure art that looks like something out of a prehistoric cave. If you thirst for knowledge, taking organic chemistry will feel like drinking from a firehose.
Indeed, I’ve heard some students complain that the weight of their organic chemistry textbook is comparable to that of a small elephant. Rest assured, though, that these complaints represent shameless exaggerations: I have yet to find an ochem text that weighs even two-thirds as much.
Nevertheless, organic chemistry does cover so much material that you can’t possibly hope to memorize it all. But good news! You don’t need to memorize the vast majority of the material if you understand the basic concepts at a fundamental level, and indeed, memorization beyond the basic rules and conventions is even frowned upon. The catch is that to really understand the concepts, you have to practice at it by working problems. Lots of problems. Lots. Did I mention the whole working problems thing? Mastering organic chemistry without working problems is impossible — kind of like trying to become a chef by reading recipes and never practicing chopping up veggies.
This workbook is for getting hands-on experience. Organic chemistry exams are a lot like a gunfight. You act with discipline only if you’ve drilled the material. Classmates who haven’t worked the problems will see the problems gunning at them on an exam and spook. They’ll come down with a bad case of exam-block, let their nerves get the better of them, and get blown to smithereens. You, on the other hand, having been to boot camp and practiced by drilling the problems, will stare the exam down like you were Wyatt Earp or Annie Oakley. When the smoke clears, you’ll emerge without a nick, and it’ll be the exam that’s carted away on a stretcher.
About This Book
Ideally, you should use this book in conjunction with some other reference book, such as a good introductory organic textbook or Organic Chemistry I For Dummies. This book doesn’t cover the material in great detail; for each section, I give a brief overview of the topic followed by problems that apply the material.
The organization of this book follows the For Dummies text, which in turn is organized to follow most organic texts fairly closely. The basic layout of this workbook is to give you straightforward problems for each section to really drill the concepts and build your confidence — before spicing things up with a mischievous humdinger or two at the end of each section to make you don the old thinking cap.
For added convenience, the book is modular, meaning you can jump around to different chapters without having to have read or worked problems in other chapters. If you need to know some other concepts to get you up to speed, just follow the cross-references.
As with all For Dummies books, I try to write the answers in a simple conversational style, just as if you and I were having a one-on-one tutoring session, coffee in hand. Here are some other conventions I follow concerning the problems:
At the beginning of each section, I present one or two example problems to show you the thought process involved in working that problem type before you take a stab at similar problems. You can refer back to the example while you’re working the other problems in that section if you get stuck.
Short answers appear in bold in the Answer Key, followed by a detailed breakdown of how I solved each problem. This includes my personal thought process of how to solve a particular problem type, such as where to start and how to proceed. Although other thought processes may lead to the same answer, my explanation can at least give you a guide for problems on which you get stuck.
Sometimes, I discuss common mistakes that people make with a certain problem type. My basic philosophy is that I’d rather over-explain than give too little explanation.
In naming molecules, I use official nomenclature of the International Union of Pure and Applied Chemistry (IUPAC).
Foolish Assumptions
When writing this book, I made a few general assumptions about you, the reader. You probably meet at least one of these assumptions:
You have a background in general chemistry, and ideally, you’ve taken a one- or two-semester course in introductory chemistry.
You’re in the midst of or are getting ready to enter your organic chemistry I class in college, and you need some extra help practicing the concepts.
You took organic chemistry a few years ago, and you want to review what you know.
No matter where you stand, this book provides multiple chances to practice organic chemistry problems in an easy-to-understand (and dare I say fun) way.
Icons Used in This Book
This book uses icons to direct you to important information. Here’s your key to these icons:
The Tip icon highlights information that can save you time and cut down on the frustration factor.
This symbol points out especially important concepts that you need to keep in mind as you work problems.
The Warning icon helps you steer clear of organic chemistry pitfalls.
This icon directs you to the examples at the beginning of each set of problems.
Beyond the Book
In addition to what you’re reading right now, this book comes with a free access-anywhere Cheat Sheet that includes handy information on the basics of organic chemistry and the periodic table of elements. To get this Cheat Sheet, simply go to www.dummies.com and type Organic Chemistry I Workbook For Dummies Cheat Sheet in the Search box.
Where to Go from Here
Organic chemistry builds on the concepts you picked up in general chemistry, so I strongly suggest starting with Chapter 1. I know, I know, you’ve already taken a class in introductory chemistry and have stuffed yourself silly with all that basic general-chemistry goodness — and that’s all in the past, man, and you’re now looking to move on to bigger and better things. However, winter breaks and days spent at the beach during summer vacations have a cruel tendency to swish the eraser around the old bean, particularly across the places that contain your vast, vast stores of chemistry knowledge. That’s why I suggest you start with Chapter 1 for a quick refresher and that you at least breeze through the rest of Part 1. In a sense, Part 1 is the most important part of the book, because if you can get the hang of drawing structures and interpreting what they mean, you’ve reached the first major milestone. Getting versed in these fundamental skills can keep you out of organic purgatory.
Of course, this book is designed to be modular, so you’re free to jump to whatever section you’re having trouble with, without having to have done the problems in a previous chapter as reference. Feel free to flip through the Table of Contents or the Index to find the topic that most interests you.
Part 1
The Fundamentals of Organic Chemistry
IN THIS PART …
You discover the words of the organic chemist — chemical structures. You start with drawing structures using the various drawing conventions and then see how you can assign charges, draw lone pairs, and predict the geometries around any atom in an organic molecule. With these basic tools under your belt, you get to resonance structures, which are patches chemists use to fix a few leaks in the Lewis structures of certain molecules. You also get to acid and base chemistry, the simplest organic reactions, and begin your mastery of depicting how reactions occur by drawing arrows to indicate the movement of electrons in a reaction.
