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Organic Chemistry I For Dummies, 2nd Edition

Book Description

The easy way to take the confusion out of organic chemistry

Organic chemistry has a long-standing reputation as a difficult course. Organic Chemistry I For Dummies takes a simple approach to the topic, allowing you to grasp concepts at your own pace.

This fun, easy-to-understand guide explains the basic principles of organic chemistry in simple terms, providing insight into the language of organic chemists, the major classes of compounds, and top trouble spots. You'll also get the nuts and bolts of tackling organic chemistry problems, from knowing where to start to spotting sneaky tricks that professors like to incorporate.

  • Refreshed example equations

  • New explanations and practical examples that reflect today's teaching methods

  • Fully worked-out organic chemistry problems

  • Baffled by benzines? Confused by carboxylic acids? Here's the help you need—in plain English!

    Table of Contents

      1. Introduction
        1. About This Book
        2. Foolish Assumptions
        3. Icons Used in This Book
        4. Beyond the Book
        5. Where to Go from Here
      2. Part I: Getting Started with Organic Chemistry
        1. Chapter 1: The Wonderful World of Organic Chemistry
          1. Shaking Hands with Organic Chemistry
          2. What Are Organic Molecules, Exactly?
          3. An Organic Chemist by Any Other Name . . .
            1. Synthetic organic chemists
            2. Bioorganic chemists
            3. Natural products chemists
            4. Physical organic chemists
            5. Organometallic chemists
            6. Computational chemists
            7. Materials chemists
        2. Chapter 2: Dissecting Atoms: Atomic Structure and Bonding
          1. Electron House Arrest: Shells and Orbitals
            1. Electron apartments: Orbitals
            2. Electron instruction manual: Electron configuration
          2. Atom Marriage: Bonding
          3. To Share or Not to Share: Ionic and Covalent Bonding
            1. Mine! They’re all mine! Ionic bonding
            2. The name’s Bond, Covalent Bond
            3. Electron piggishness and electronegativity
          4. Separating Charge: Dipole Moments
            1. Problem solving: Predicting bond dipole moments
            2. Problem solving: Predicting molecule dipole moments
          5. Seeing Molecular Geometries
            1. Mixing things up: Hybrid orbitals
            2. Predicting hybridization for atoms
          6. It’s All Greek to Me: Sigma and Pi Bonding
        3. Chapter 3: Speaking with Pictures: Drawing Structures
          1. Picture-Talk: Lewis Structures
            1. Taking charge: Assigning formal charges
            2. Drawing structures
            3. Atom packing: Condensed structures
            4. Structural shorthand: Line-bond structures
            5. Converting Lewis structures to line-bond structures
            6. Determining the number of hydrogens on line-bond structures
            7. So lonely: Determining lone pairs on atoms
          2. Problem Solving: Arrow Pushing
          3. Drawing Resonance Structures
            1. Rules for resonance structures
            2. Problem solving: Drawing resonance structures
            3. Drawing more than two resonance structures
            4. Assigning importance to resonance structures
            5. Common mistakes in drawing resonance structures
        4. Chapter 4: Covering the Bases (And the Acids)
          1. A Defining Moment: Acid-Base Definitions
            1. Arrhenius acids and bases: A little watery
            2. Pulling for protons: Brønsted-Lowry acids and bases
            3. Electron lovers and haters: Lewis acids and bases
          2. Comparing Acidities of Organic Molecules
            1. Comparing atoms
            2. Seeing atom hybridization
            3. Seeing electronegativity effects
            4. Seeing resonance effects
          3. Defining pKa: A Quantitative Scale of Acidity
          4. Problem Solving: Predicting the Direction of Acid-Base Reactions at Equilibrium
        5. Chapter 5: Reactivity Centers: Functional Groups
          1. Hydrocarbons
            1. Double the fun: The alkenes
            2. Alkynes of fun
            3. Smelly compounds: The aromatics
          2. Singly Bonded Heteroatoms
            1. Happy halides
            2. For rubbing and drinking: Alcohols
            3. What stinks? Thiols
            4. How ethereal
          3. Carbonyl Compounds
            1. Living on the edge: Aldehydes
            2. Stuck in the middle: Ketones
            3. Carboxylic acids
            4. Sweet-smelling compounds: Esters
            5. Nitrogen-containing functional groups
            6. I am what I amide
            7. Be nice, don’t be amine person
            8. Nitriles
          4. Test Your Knowledge
        6. Chapter 6: Seeing in 3-D: Stereochemistry
          1. Drawing Molecules in 3-D
          2. Comparing Stereoisomers and Constitutional Isomers
          3. Mirror Image Molecules: Enantiomers
          4. Seeing Chiral Centers
          5. Assigning Configurations to Chiral Centers: The R/S Nomenclature
          6. Problem Solving: Determining R/S Configuration
            1. Step 1: Prioritizing the substituents
            2. Step 2: Putting the number-four substituent in the back
            3. Step 3: Drawing the curve
          7. The Consequences of Symmetry: Meso Compounds
          8. Rotating Plane-Polarized Light
          9. Multiple Chiral Centers: Diastereomers
          10. Representing 3-D Structures on Paper: Fischer Projections
            1. Rules for using Fischer projections
            2. Determining R/S configuration from a Fischer projection
            3. Seeing stereoisomerism with Fischer projections
            4. Spotting meso compounds with Fischer projections
          11. Keeping the Jargon Straight
      3. Part II: Hydrocarbons
        1. Chapter 7: What’s in a Name? Alkane Nomenclature
          1. All in a Line: Straight-Chain Alkanes
          2. Reaching Out: Branching Alkanes
          3. Finding the longest chain
          4. Numbering the chain
          5. Seeing the substituents
          6. Ordering the substituents
          7. More than one of a kind
          8. Naming complex substituents
        2. Chapter 8: Drawing Alkanes
          1. Converting a Name to a Structure
          2. Conformation of Straight-Chain Alkanes
            1. Newman! Conformational analysis and Newman projections
            2. Conformations of butane
          3. Full Circle: Cycloalkanes
            1. The stereochemistry of cycloalkanes
            2. Conformations of cyclohexane
          4. Problem Solving: Drawing the Most Stable Chair Conformation
          5. Reacting Alkanes: Free-Radical Halogenation
            1. Getting things started: Initiation
            2. Keeping the reaction going: Propagation
            3. You’re fired: Termination steps
            4. Selectivity of chlorination and bromination
        3. Chapter 9: Seeing Double: The Alkenes
          1. Defining Alkenes
          2. Taking Away Hydrogens: Degrees of Unsaturation
            1. Determining degrees of unsaturation from a structure
            2. Problem solving: Determining degrees of unsaturation from a molecular formula
          3. The Nomenclature of Alkenes
            1. Numbering the parent chain
            2. Adding multiple double bonds
            3. Common names of alkenes
          4. The Stereochemistry of Alkenes
            1. You on my side or their side? Cis and trans stereochemistry
            2. Playing a game of high-low: E/Z stereochemistry
          5. Stabilities of Alkenes
            1. Alkene substitution
            2. Stability of cis and trans isomers
          6. Formation of Alkenes
            1. Elimination of acid: Dehydrohalogenation
            2. Losing water: Dehydration of alcohols
            3. Alkenes from coupling: The Wittig reaction
        4. Chapter 10: Reactions of Alkenes
          1. Adding Hydrohalic Acids across Double Bonds
          2. I’m Positive: Carbocations
            1. Helping a neighbor: Hyperconjugation
            2. Resonance stabilization of carbocations
            3. Carbocation mischief: Rearrangements
          3. Adding Water across Double Bonds
            1. Markovnikov addition: Oxymercuration-demercuration
            2. Anti-Markovnikov addition: Hydroboration
            3. A double shot: Dihydroxylation
            4. Double the fun: Bromination
          4. Chopping Up Double Bonds: Ozonolysis
          5. Double-Bond Cleavage: Permanganate Oxidation
          6. Making Cyclopropanes with Carbenes
          7. Making Cyclopropanes: The Simmons–Smith Reaction
          8. Making Epoxides
          9. Adding Hydrogen: Hydrogenation
        5. Chapter 11: It Takes Alkynes: The Carbon-Carbon Triple Bond
          1. Naming Alkynes
          2. Seeing Alkyne Orbitals
          3. Alkynes in Rings
          4. Making Alkynes
            1. Losing two: Dehydrohalogenation
            2. Coupling alkynes: Acetylide chemistry
            3. Brominating alkynes: Double the fun
            4. Saturating alkynes with hydrogen
            5. Adding one hydrogen molecule to alkynes
            6. Oxymercuration of alkynes
            7. Hydroboration of alkynes
      4. Part III: Functional Groups
        1. Chapter 12: Replacing and Removing: Substitution and Elimination Reactions
          1. Group Swap: Substitution Reactions
          2. Seeing Second-Order Substitution: The S<sub xmlns="" xmlns:epub="">N</sub>2 Mechanism2 Mechanism
            1. How fast? The rate equation for the S<sub xmlns="" xmlns:epub="">N</sub>2 reaction2 reaction
            2. Effect of the substrate on the S<sub xmlns="" xmlns:epub="">N</sub>2 reaction2 reaction
            3. Needs nucleus: The role of the nucleophile
            4. Seeing the S<sub xmlns="" xmlns:epub="">N</sub>2 reaction in 3-D: Stereochemistry2 reaction in 3-D: Stereochemistry
            5. Seeing solvent effects
            6. I’m outta here: The leaving group
          3. First-Order Substitution: The S<sub xmlns="" xmlns:epub="">N</sub>1 Reaction1 Reaction
            1. How fast? The rate equation for the S<sub xmlns="" xmlns:epub="">N</sub>1 reaction1 reaction
            2. Seeing good S<sub xmlns="" xmlns:epub="">N</sub>1 substrates1 substrates
            3. Seeing solvent effects on the S<sub xmlns="" xmlns:epub="">N</sub>1 reaction1 reaction
            4. Stereochemistry of the S<sub xmlns="" xmlns:epub="">N</sub>1 reaction1 reaction
            5. Other fun facts about the S<sub xmlns="" xmlns:epub="">N</sub>1 reaction1 reaction
          4. Seeing Elimination Reactions
            1. Seeing second-order eliminations: The E2 reaction
            2. Seeing first-order elimination: The E1 reaction
          5. Help! Distinguishing Substitution from Elimination
        2. Chapter 13: Getting Drunk on Organic Molecules: The Alcohols
          1. Classifying Alcohols
          2. An Alcohol by Any Other Name: Naming Alcohols
          3. Alcohol-Making Reactions
            1. Adding water across double bonds
            2. Reduction of carbonyl compounds
            3. The Grignard reaction
          4. Reactions of Alcohols
            1. Losing water: Dehydration
            2. Making ethers: Williamson ether synthesis
            3. Oxidation of alcohols
        3. Chapter 14: Side-by-Side: Conjugated Alkenes and the Diels–Alder Reaction
          1. Seeing Conjugated Double Bonds
          2. Addition of Hydrohalic Acids to Conjugated Alkenes
            1. Seeing the reaction diagram of conjugate addition
            2. Comparing kinetics and thermodynamics of conjugate addition
          3. The Diels–Alder Reaction
            1. Seeing the diene and the dienophile
            2. The stereochemistry of addition
            3. Seeing bicyclic products
          4. Problem Solving: Determining Products of Diels–Alder Reactions
        4. Chapter 15: Lord of the Rings: Aromatic Compounds
          1. Defining Aromatic Compounds
            1. The structure of benzene
            2. Diversity of aromatic compounds
            3. So, what exactly makes a molecule aromatic?
            4. Hückel’s 4n + 2 rule
          2. Explaining Aromaticity: Molecular Orbital Theory
            1. What the heck is molecular orbital theory?
            2. Making molecular orbital diagrams
            3. Two rings diverged in a wood: Frost circles
            4. Making the molecular orbital diagram of benzene
            5. Seeing the molecular orbitals of benzene
            6. Making the molecular orbital diagram of cyclobutadiene
          3. Problem Solving: Determining Aromaticity
          4. Problem Solving: Predicting Acidities and Basicities
            1. Comparing acidities
            2. Comparing basicities
          5. Naming Benzenes and Aromatics
            1. Common names of substituted benzenes
            2. Names of common aromatics
        5. Chapter 16: Bringing Out the Howitzers: Reactions of Aromatic Compounds
          1. Electrophilic Aromatic Substitution of Benzene
            1. Adding alkyl substituents: Friedel–Crafts alkylation
            2. Overcoming adversity: Friedel–Crafts acylation
            3. Reducing nitro groups
            4. Oxidation of alkylated benzenes
          2. Adding Two: Synthesis of Disubstituted Benzenes
            1. Electron donors: Ortho-para activators
            2. Electron-withdrawing groups: Meta directors
          3. Problem Solving: Synthesis of Substituted Benzenes
          4. Nucleophiles Attack! Nucleophilic Aromatic Substitution
      5. Part IV: Spectroscopy and Structure Determination
        1. Chapter 17: A Smashing Time: Mass Spectrometry
          1. Defining Mass Spectrometry
          2. Taking Apart a Mass Spectrometer
            1. The inlet
            2. Electron ionization: The smasher
            3. The sorter and weigher
            4. Detector and spectrum
          3. The Mass Spectrum
          4. Kind and Caring: Sensitivity of Mass Spec
          5. Resolving the Problem: Resolution
          6. Changing the Weight: Isotopes
          7. The Nitrogen Rule
          8. Identifying Common Fragmentation Patterns
            1. Smashing alkanes
            2. Breaking next to a heteroatom: Alpha cleavage
            3. Loss of water: Alcohols
            4. Rearranging carbonyls: The McLafferty rearrangement
            5. Breaking benzenes and double bonds
            6. Self test: Working the problem
          9. Key Ideas Checklist
        2. Chapter 18: Seeing Good Vibrations: IR Spectroscopy
          1. Bond Calisthenics: Infrared Absorption
            1. Applying Hooke’s law to molecules
            2. Seeing bond vibration and IR light absorption
            3. Seeing absorption intensity
            4. IR forbidden stretches
          2. Dissecting an IR Spectrum
          3. Identifying the Functional Groups
            1. Sizing up the IR spectrum
            2. Recognizing functional groups
          4. Seeing to the Left of the C-H Absorptions
            1. Big and fat: The alcohols
            2. Milking the spectrum: Amines
          5. Seeing to the Right of the C-H Absorptions
            1. Big and tall: Carbonyl groups
            2. Hydrocarbon stretches: Alkenes, alkynes, and aromatics
        3. Chapter 19: NMR Spectroscopy: Hold onto Your Hats, You’re Going Nuclear!
          1. Why NMR?
          2. How NMR Works
            1. Giant magnets and molecules: NMR theory
            2. Grab your jackets: Electron shielding
          3. The NMR Spectrum
            1. Standardizing chemical shifts
            2. Seeing symmetry and chemical equivalency
          4. The NMR Spectrum Manual: Dissecting the Pieces
            1. Seeing the chemical shift
            2. Incorporating the integration
            3. Catching on to coupling
          5. Considering Carbon NMR
          6. Checklist: Putting the Pieces Together
        4. Chapter 20: Following the Clues: Solving Problems in NMR
          1. Follow the Clues
            1. Clue 1: Determine the degrees of unsaturation from the molecular formula
            2. Clue 2: Look at the IR spectrum to determine the major functional groups present in the unknown compound
            3. Clue 3: Determine the peak ratios by measuring the heights of the integration curves
            4. Clue 4: Break the NMR peaks into fragments using the integration from Clue 3
            5. Clue 5: Combine the fragments in a way that fits with the NMR peak splitting, the chemical shift, and the degrees of unsaturation
            6. Clue 6: Recheck your structure with the NMR and the IR spectrum to make sure it’s an exact match
          2. Working Problems
            1. Example 1: Using the molecular formula and NMR to deduce the structure of a molecule
            2. Example 2: Using the molecular formula, IR, and NMR to deduce the structure of a molecule
          3. Three Common Mistakes in NMR Problem Solving
            1. Mistake #1: Trying to determine a structure from the chemical shift
            2. Mistake #2: Starting with coupling
            3. Mistake #3: Confusing integration with coupling
      6. Part V: The Part of Tens
        1. Chapter 21: Ten (Or So) Great Organic Chemists
          1. August Kekulé
          2. Friedrich Wöhler
          3. Archibald Scott Couper
          4. Johan Josef Loschmidt
          5. Louis Pasteur
          6. Emil Fischer
          7. Percy Julian
          8. Robert Burns Woodward
          9. Linus Pauling
          10. Dorothy Hodgkin
          11. John Pople
        2. Chapter 22: Ten Cool Organic Discoveries
          1. Explosives and Dynamite!
          2. Fermentation
          3. The Synthesis of Urea
          4. The Handedness of Tartaric Acid
          5. Diels–Alder Reaction
          6. Buckyballs
          7. Soap
          8. Aspartame
          9. Penicillin
          10. Teflon
        3. Chapter 23: Ten Cool Organic Molecules
          1. Octanitrocubane
          2. Fenestrane
          3. Carbon Nanotubes
          4. Bullvalene
          5. The Norbornyl Cation
          6. Capsaicin
          7. Indigo
          8. Maitotoxin
          9. Molecular Cages
          10. Fucitol
      7. Part VI: Appendixes
        1. Appendix A: Working Multistep Synthesis Problems
          1. Why Multistep Synthesis?
          2. The Five Commandments
            1. Commandment 1: Thou shalt learn thy reactions
            2. Commandment 2: Thou shalt compare carbon skeletons
            3. Commandment 3: Thou shalt work backward
            4. Commandment 4: Thou shalt check thyne answer
            5. Commandment 5: Thou shalt work many problems
        2. Appendix B: Working Reaction Mechanisms
          1. The Two Unspoken Mechanism Types
          2. Do’s and Don’ts for Working Mechanisms
          3. Types of Mechanisms
        3. Appendix C: Glossary
      8. About the Author
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