Organic chemistry I for dummies

About This Book

Foolish Assumptions

Icons Used in This Book

Beyond the Book

Where to Go from Here

pt. I Getting Started With Organic Chemistry

ch. 1 The Wonderful World of Organic Chemistry

Shaking Hands with Organic Chemistry

What Are Organic Molecules, Exactly?

An Organic Chemist by Any Other Name

Synthetic organic chemists

Bioorganic chemists

Natural products chemists

Physical organic chemists

Organometallic chemists

Computational chemists

Materials chemists

ch. 2 Dissecting Atoms: Atomic Structure and Bonding

Electron House Arrest: Shells and Orbitals

Electron apartments: Orbitals

Electron instruction manual: Electron configuration

Atom Marriage: Bonding

To Share or Not to Share: Ionic and Covalent Bonding

Mine! They're all mine! Ionic bonding

The name's Bond, Covalent Bond

Electron piggishness and electronegativity

Separating Charge: Dipole Moments.

Problem solving: Predicting bond dipole moments

Problem solving: Predicting molecule dipole moments

Seeing Molecular Geometries

Mixing things up: Hybrid orbitals

Predicting hybridization for atoms

It's All Greek to Me: Sigma and Pi Bonding

ch. 3 Speaking with Pictures: Drawing Structures

Picture-Talk: Lewis Structures

Taking charge: Assigning formal charges

Drawing structures

Atom packing: Condensed structures

Structural shorthand: Line-bond structures

Converting Lewis structures to line-bond structures

Determining the number of hydrogens on line-bond structures

So lonely: Determining lone pairs on atoms

Problem Solving: Arrow Pushing

Drawing Resonance Structures

Rules for resonance structures

Problem solving: Drawing resonance structures

Drawing more than two resonance structures

Assigning importance to resonance structures

Common mistakes in drawing resonance structures.

ch. 4 Covering the Bases (And the Acids)

A Defining Moment: Acid-Base Definitions

Arrhenius acids and bases: A little watery

Pulling for protons: Br©ınsted-Lowry acids and bases

Electron lovers and haters: Lewis acids and bases

Comparing Acidities of Organic Molecules

Comparing atoms

Seeing atom hybridization

Seeing electronegativity effects

Seeing resonance effects

Defining pKa: A Quantitative Scale of Acidity

Problem Solving: Predicting the Direction of Acid-Base Reactions at Equilibrium

ch. 5 Reactivity Centers: Functional Groups

Hydrocarbons

Double the fun: The alkenes

Alkynes of fun

Smelly compounds: The aromatics

Singly Bonded Heteroatoms

Happy halides

For rubbing and drinking: Alcohols

What stinks? Thiols

How ethereal

Carbonyl Compounds

Living on the edge: Aldehydes

Stuck in the middle: Ketones

Carboxylic acids

Sweet-smelling compounds: Esters.

Nitrogen-containing functional groups

I am what I amide

Be nice, don't be amine person

Nitriles

Test Your Knowledge

ch. 6 Seeing in 3-D: Stereochemistry

Drawing Molecules in 3-D

Comparing Stereoisomers and Constitutional Isomers

Mirror Image Molecules: Enantiomers

Seeing Chiral Centers

Assigning Configurations to Chiral Centers: The R/S Nomenclature

Problem Solving: Determining R/S Configuration

Step 1 Prioritizing the substituents

Step 2 Putting the number-four substituent in the back

Step 3 Drawing the curve

The Consequences of Symmetry: Meso Compounds

Rotating Plane-Polarized Light

Multiple Chiral Centers: Diastereomers

Representing 3-D Structures on Paper: Fischer Projections

Rules for using Fischer projections

Determining R/S configuration from a Fischer projection

Seeing stereoisomerism with Fischer projections

Spotting meso compounds with Fischer projections.

Keeping the Jargon Straight

pt. II Hydrocarbons

ch. 7 What's in a Name? Alkane Nomenclature

All in a Line: Straight-Chain Alkanes

Reaching Out: Branching Alkanes

Finding the longest chain

Numbering the chain

Seeing the substituents

Ordering the substituents

More than one of a kind

Naming complex substituents

ch. 8 Drawing Alkanes

Converting a Name to a Structure

Conformation of Straight-Chain Alkanes

Newman! Conformational analysis and Newman projections

Conformations of butane

Full Circle: Cycloalkanes

The stereochemistry of cycloalkanes

Conformations of cyclohexane

Problem Solving: Drawing the Most Stable Chair Conformation

Reacting Alkanes: Free-Radical Halogenation

Getting things started: Initiation

Keeping the reaction going: Propagation

You're fired: Termination steps

Selectivity of chlorination and bromination

ch. 9 Seeing Double: The Alkenes

Defining Alkenes.

Taking Away Hydrogens: Degrees of Unsaturation

Determining degrees of unsaturation from a structure

Problem solving: Determining degrees of unsaturation from a molecular formula

The Nomenclature of Alkenes

Numbering the parent chain

Adding multiple double bonds

Common names of alkenes

The Stereochemistry of Alkenes

You on my side or their side? Cis and trans stereochemistry

Playing a game of high-low: E/Z stereochemistry

Stabilities of Alkenes

Alkene substitution

Stability of cis and trans isomers

Formation of Alkenes

Elimination of acid: Dehydrohalogenation

Losing water: Dehydration of alcohols

Alkenes from coupling: The Wittig reaction

ch. 10 Reactions of Alkenes

Adding Hydrohalic Acids across Double Bonds

I'm Positive: Carbocations

Helping a neighbor: Hyperconjugation

Resonance stabilization of carbocations

Carbocation mischief: Rearrangements

Adding Water across Double Bonds.

Markovnikov addition: Oxymercuration-demercuration

Anti-Markovnikov addition: Hydroboration

A double shot: Dihydroxylation

Double the fun: Bromination

Chopping Up Double Bonds: Ozonolysis

Double-Bond Cleavage: Permanganate Oxidation

Making Cyclopropanes with Carbenes

Making Cyclopropanes: The Simmons-Smith Reaction

Making Epoxides

Adding Hydrogen: Hydrogenation

ch. 11 It Takes Alkynes: The Carbon-Carbon Triple Bond

Naming Alkynes

Seeing Alkyne Orbitals

Alkynes in Rings

Making Alkynes

Losing two: Dehydrohalogenation

Coupling alkynes: Acetylide chemistry

Brominating alkynes: Double the fun

Saturating alkynes with hydrogen

Adding one hydrogen molecule to alkynes

Oxymercuration of alkynes

Hydroboration of alkynes

pt. III Functional Groups

ch. 12 Replacing and Removing: Substitution and Elimination Reactions

Group Swap: Substitution Reactions.

Seeing Second-Order Substitution: The SN2 Mechanism

How fast? The rate equation for the SN2 reaction

Effect of the substrate on the SN2 reaction

Needs nucleus: The role of the nucleophile

Seeing the SN2 reaction in 3-D: Stereochemistry

Seeing solvent effects

I'm outta here: The leaving group

First-Order Substitution: The SN1 Reaction

How fast? The rate equation for the SN1 reaction

Seeing good SN1 substrates

Seeing solvent effects on the SN1 reaction

Stereochemistry of the SN1 reaction

Other fun facts about the SN1 reaction

Seeing Elimination Reactions

Seeing second-order eliminations: The E2 reaction

Seeing first-order elimination: The E1 reaction

Help! Distinguishing Substitution from Elimination

ch. 13 Getting Drunk on Organic Molecules: The Alcohols

Classifying Alcohols

An Alcohol by Any Other Name: Naming Alcohols

Alcohol-Making Reactions

Adding water across double bonds.

Reduction of carbonyl compounds

The Grignard reaction

Reactions of Alcohols

Losing water: Dehydration

Making ethers: Williamson ether synthesis

Oxidation of alcohols

ch. 14 Side-by-Side: Conjugated Alkenes and the Diels

Alder Reaction

Seeing Conjugated Double Bonds

Addition of Hydrohalic Acids to Conjugated Alkenes

Seeing the reaction diagram of conjugate addition

Comparing kinetics and thermodynamics of conjugate addition

The Diels

Alder Reaction

Seeing the diene and the dienophile

The stereochemistry of addition

Seeing bicyclic products

Problem Solving: Determining Products of Diels

Alder Reactions

ch. 15 Lord of the Rings: Aromatic Compounds

Defining Aromatic Compounds

The structure of benzene

Diversity of aromatic compounds

So, what exactly makes a molecule aromatic?

Huckel's 4n + 2 rule

Explaining Aromaticity: Molecular Orbital Theory

What the heck is molecular orbital theory?

Making molecular orbital diagrams

Two rings diverged in a wood: Frost circles

Making the molecular orbital diagram of benzene

Seeing the molecular orbitals of benzene

Making the molecular orbital diagram of cyclobutadiene

Problem Solving: Determining Aromaticity

Problem Solving: Predicting Acidities and Basicities

Comparing acidities

Comparing basicities

Naming Benzenes and Aromatics

Common names of substituted benzenes

Names of common aromatics

ch. 16 Bringing Out the Howitzers: Reactions of Aromatic Compounds

Electrophilic Aromatic Substitution of Benzene

Adding alkyl substituents: Friedel

Crafts alkylation

Overcoming adversity: Friedel

Crafts acylation

Reducing nitro groups

Oxidation of alkylated benzenes

Adding Two: Synthesis of Disubstituted Benzenes

Electron donors: Ortho-para activators

Electron-withdrawing groups: Meta directors

Problem Solving: Synthesis of Substituted Benzenes.

Nucleophiles Attack! Nucleophilic Aromatic Substitution

pt. IV Spectroscopy and Structure Determination

ch. 17 A Smashing Time: Mass Spectrometry

Defining Mass Spectrometry

Taking Apart a Mass Spectrometer

The inlet

Electron ionization: The smasher

The sorter and weigher

Detector and spectrum

The Mass Spectrum

Kind and Caring: Sensitivity of Mass Spec

Resolving the Problem: Resolution

Changing the Weight: Isotopes

The Nitrogen Rule

Identifying Common Fragmentation Patterns

Smashing alkanes

Breaking next to a heteroatom: Alpha cleavage

Loss of water: Alcohols

Rearranging carbonyls: The McLafferty rearrangement

Breaking benzenes and double bonds

Self test: Working the problem

Key Ideas Checklist

ch. 18 Seeing Good Vibrations: IR Spectroscopy

Bond Calisthenics: Infrared Absorption

Applying Hooke's law to molecules

Seeing bond vibration and IR light absorption.

Seeing absorption intensity

IR forbidden stretches

Dissecting an IR Spectrum

Identifying the Functional Groups

Sizing up the IR spectrum

Recognizing functional groups

Seeing to the Left of the C-H Absorptions

Big and fat: The alcohols

Milking the spectrum: Amines

Seeing to the Right of the C-H Absorptions

Big and tall: Carbonyl groups

Hydrocarbon stretches: Alkenes, alkynes, and aromatics

ch. 19 NMR Spectroscopy: Hold onto Your Hats, You're Going Nuclear!

Why NMR?

How NMR Works

Giant magnets and molecules: NMR theory

Grab your jackets: Electron shielding

The NMR Spectrum

Standardizing chemical shifts

Seeing symmetry and chemical equivalency

The NMR Spectrum Manual: Dissecting the Pieces

Seeing the chemical shift

Incorporating the integration

Catching on to coupling

Considering Carbon NMR

Checklist: Putting the Pieces Together.

ch. 20 Following the Clues: Solving Problems in NMR

Follow the Clues

Clue 1 Determine the degrees of unsaturation from the molecular formula

Clue 2 Look at the IR spectrum to determine the major functional groups present in the unknown compound

Clue 3 Determine the peak ratios by measuring the heights of the integration curves

Clue 4 Break the NMR peaks into fragments using the integration from Clue 3

Clue 5 Combine the fragments in a way that fits with the NMR peak splitting, the chemical shift, and the degrees of unsaturation

Clue 6 Recheck your structure with the NMR and the IR spectrum to make sure it's an exact match

Working Problems

Example 1 Using the molecular formula and NMR to deduce the structure of a molecule

Example 2 Using the molecular formula, IR, and NMR to deduce the structure of a molecule

Three Common Mistakes in NMR Problem Solving.

Mistake #1 Trying to determine a structure from the chemical shift

Mistake #2 Starting with coupling

Mistake #3 Confusing integration with coupling

pt. V The Part of Tens

ch. 21 Ten (Or So) Great Organic Chemists

August Kekule

Friedrich Wohler

Archibald Scott Couper

Johan Josef Loschmidt

Louis Pasteur

Emil Fischer

Percy Julian

Robert Burns Woodward

Linus Pauling

Dorothy Hodgkin

John Pople

ch. 22 Ten Cool Organic Discoveries

Explosives and Dynamite!

Fermentation

The Synthesis of Urea

The Handedness of Tartaric Acid

Diels

Alder Reaction

Buckyballs

Soap

Aspartame

Penicillin

Teflon

ch. 23 Ten Cool Organic Molecules

Octanitrocubane

Fenestrane

Carbon Nanotubes

Bullvalene

The Norbornyl Cation

Capsaicin

Indigo

Maitotoxin

Molecular Cages

Fucitol

Par VI Appendixes

Appendix A Working Multistep Synthesis Problems

Why Multistep Synthesis?

Five Commandments

Commandment 1 Thou shalt learn thy reactions

Commandment 2 Thou shalt compare carbon skeletons

Commandment 3 Thou shalt work backward

Commandment 4 Thou shalt check thyne answer

Commandment 5 Thou shalt work many problems

Appendix B Working Reaction Mechanisms

The Two Unspoken Mechanism Types

Do's and Don'ts for Working Mechanisms

Types of Mechanisms

Appendix C Glossary.