Organic Chemistry I Workbook

Title Page
Copyright Page
Table of Contents
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
			Bronsted-Lowry acids and bases
			Lewis acids and bases
		Comparing Acidities of Organic Molecules
			Contrasting atom electronegativity, size, and hybridization
			The effect of nearby atoms
			Resonance effects
		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 H2O 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 SN1 and SN2 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
EULA