Organic Chemistry II For Dummies

Title Page
Copyright Page
Table of Contents
Introduction
	About This Book
	Conventions Used in This Book
	Foolish Assumptions
	Icons Used in This Book
	Beyond the Book
	Where to Go from Here
Part 1 Brushing Up on Important Organic Chemistry I Concepts
	Chapter 1 Organic Chemistry II: Here We Go Again!
		Recapping Organic Chemistry I
			Intermolecular forces
			Functional groups
			Reactions
			Spectroscopy
			Isomerism and optical activity
				Cis-trans isomers
				Chiral compounds
		Looking Ahead to Organic Chemistry II
	Chapter 2 Remembering How We Do It: Mechanisms
		Duck — Here Come the Arrows
		Coming Around to Curved Arrows
		Getting Ready for Some Basic Moves
			Bond → lone pair
			Bond → bond
			Lone pair → bond
		Combining the Basic Moves
			Intermediates
			Keys to substitution and elimination mechanisms
		Revisiting Free-Radical Mechanisms
	Chapter 3 Alcohols and Ethers: Not Just for Drinking and Sleeping
		Getting Acquainted with Alcohols
			Structure and nomenclature of alcohols
				Classifying alcohols
				Naming alcohols
			Physical properties of alcohols
				Melting and boiling points
				Solubility and density
			Making moonshine: Synthesis of alcohols
				Hydration of alkenes
				Catalytic hydration of alkenes
				Oxymercuration-demercuration reactions with alkenes
				Hydroboration-oxidation reactions with alkenes
				Diols from reactions with alkenes
				Preparation of alcohols by the reduction of carbonyls
				Grignard reagents and production of alcohols
			What will they do besides burn? Reactions of alcohols
				Dehydration of alcohols (–H2O)
				Oxidation of alcohols
				Conversion of alcohols to esters
				Reaction of alcohols as acids
				Conversion of alcohols to alkyl halides
		Introducing Ether (Not the Ether Bunny)
			Structure and nomenclature of ethers
			Sleepy time: Physical properties of ethers
				Melting and boiling points
				Solubility
			Synthesis of ethers
			Reactions of ethers
				Acidic cleavage of ethers
				Sulfuric acid and ethers
				Reactions of epoxides
		Summarizing the Spectra of Alcohols and Ethers
	Chapter 4 Conjugated Unsaturated Systems
		When You Don’t Have Enough: Unsaturated Systems
			Conjugated systems
			The allylic radical
			Butadiene
		Delocalization and Resonance
			Resonance rules
			Stability of conjugated unsaturated systems
		Reactions of Conjugated Unsaturated Systems
			Put in the second string: Substitution reactions
				The mechanism
				Understanding the reaction
				Allylic bromination
			Electrophilic addition
				The mechanism
				Understanding the reaction
			More than a tree: Diels-Alder reactions
				Conditions
				Stereochemistry
		Passing an Exam with Diels-Adler Questions
			Identifying the product
			Identifying the reactants
	Chapter 5 “Seeing” Molecules: Spectroscopy Revisited
		Chemical Fingerprints: Infrared Spectroscopy
			Double bonds
			Triple bonds
			O-H and N-H stretches
			C-H stretches
		Suntans and Beyond: Ultraviolet and Visible Spectroscopy
		Not Weight Watchers, Mass Watchers: Mass Spectroscopy
			The molecular ion
			Fragmentation
		No Glowing Here: NMR Spectroscopy
			Proton
				Integration
				Coupling
			Carbon-13
Part 2 Discovering Aromatic (And Not So Aromatic) Compounds
	Chapter 6 Introducing Aromatics
		Benzene: Where It All Starts
			Figuring out benzene’s structure
			Understanding benzene’s resonance
			The stability of benzene
			Physical properties of benzene
			Organic math — Hückel’s Rule
			Other aromatics
		Smelly Relatives: The Aromatic Family
			Nomenclature of the aromatic family
			Derivatives of benzene
			Branches of aromatic groups
		Black Sheep of the Family: Heterocyclic Aromatic Compounds
			Aromatic nitrogen compounds
			Aromatic oxygen and sulfur compounds
		Spectroscopy of Aromatic Compounds
			IR
			UV-vis
			NMR
			Mass spec
	Chapter 7 Aromatic Substitution Part I: Attack of the Electrophiles
		Basics of Electrophilic Substitution Reactions
		Reactions of Benzene
			Halogenation of benzene
			Nitration of benzene
			Sulfonation of benzene
		Friedel-Crafts Reactions
			Alkylation
			Acylation
		Why Do an Alkylation?
		Changing Things: Modifying the Reactivity of an Aromatic
			Lights, camera, action: Directing
				Making a difference with the substituent
				Making predictions
			Turning it on, turning it off: Activating and deactivating
			Steric hindrance
		Limitations of Electrophilic Substitution Reactions
	Chapter 8 Aromatic Substitution Part II: Attack of the Nucleophiles and Other Reactions
		Coming Back to Nucleophilic Substitution Reactions
		Mastering the Mechanisms of Nucleophilic Substitution Reactions
		Losing and Gaining: Mechanisms of Elimination/Addition Reactions
			Benzyne
			The elimination/addition mechanism
		Synthetic Strategies for Making Aromatic Compounds
		Briefly Exploring Other Reactions
Part 3 Carbonyls: Good Alcohols Gone Bad
	Chapter 9 Comprehending Carbonyls
		Carbonyl Basics
			Considering compounds containing the carbonyl group
				Aldehyde and ketones
				Carboxylic acids
				Acyl group
				Acyl chlorides
				Acid anhydride
				Esters
				Amides
			Getting to know the acidic carbonyl
		Polarity of Carbonyls
		Resonance in Carbonyls
		Reactivity of the Carbonyl Group
		Spectroscopy of Carbonyls
			Infrared spectroscopy
			Ultraviolet-visible (electronic) spectroscopy
			Nuclear magnetic resonance (NMR) spectroscopy
				Proton NMR
				13C NMR
			Mass spectroscopy
	Chapter 10 Aldehydes and Ketones
		Meeting Alcohol’s Relatives: Structure and Nomenclature
		Defining Physical Properties of Aldehydes and Ketones
		Creating Aldehydes and Ketones with Synthesis Reactions
			Oxidation reactions
			Reduction reactions
			Other reactions
				Beginning with an alkyne
				Utilizing Friedel-Crafts acylation
				Creating ketones two ways with organic nitriles
				Forming from carboxylic acid
		Taking Them a Step Further: Reactions of Aldehydes and Ketones
			Nucleophilic attack of aldehydes and ketones
				Oxygen-containing nucleophiles
				Nitrogen-containing nucleophiles
				Carbon-containing nucleophiles
			Oxidation of aldehydes and ketones
				Aldehydes
				Ketones
			The Baeyer-Villiger reaction
		Checking Out Spectroscopy Specs
	Chapter 11 Enols and Enolates
		Getting to Know Enols and Enolates
			Enough already: Structure of enols and enolates
			I thought I saw a tautomer
		Studying the Synthesis of Enols and Enolates
		Thinking Through Reactions of Enols and Enolates
			Haloform reactions
			Aldol reactions and condensations
				Crossed aldol condensations
				Aldol cyclization
			Addition reactions to unsaturated aldehydes and ketones
				Claisen-Schmidt reaction
				Michael addition
			Other enolate-related reactions
				Nitroalkanes
				Nitriles
			Miscellaneous reactions
				Other additions
				Cannizzaro reaction
				Acid catalysis
				Robinson annulation
	Chapter 12 Carboxylic Acids and Their Derivatives
		Seeing the Structure and Nomenclature of Carboxylic Acids and Derivatives
			Structure
			Nomenclature
				Finding out what carboxylic acids are called
				Designating dicarboxylic acids
				Examining the nomenclature of esters
				Naming acid anhydrides
				Labeling acyl chlorides
				Clarifying amide nomenclature
		Checking Out Some Physical Properties of Carboxylic Acids and Derivatives
			Carboxylic acids
			Esters
			Amides
		Considering the Acidity of Carboxylic Acids
		Determining How Carboxylic Acids and Derivatives Are Synthesized
			Synthesizing carboxylic acids
				Oxidation of alkenes
				Oxidation of aldehydes and primary alcohols
				Oxidation of alkyl benzenes
				Oxidation of methyl ketones
				Hydrolysis of cyanohydrins and other nitriles
				Carbonation of Grignard reagents
			Developing acyl halides with halogen
			Removing water to form acid anhydrides
				Sodium salt plus acid chloride
				Acid plus acid chloride plus pyridine
				Acetic anhydride plus acid
				Cyclic anhydrides
			Uniting acids and alcohols to make esters
				Acid plus alcohol
				Acid chloride plus alcohol
				Acid anhydride plus an alcohol
				Transesterification
				Methyl esters from diazomethane
			Bringing acids and bases together to create amides
				From acid chlorides
				From acid anhydrides
				From esters
				From carboxylic acids and ammonium salts
		Exploring Reactions
			Generous carboxylic acids
			Simple acyl halide and anhydride reactions
			Hydrolysis of esters
				Acid hydrolysis
				Base hydrolysis (saponification)
			Amide reactions, ester’s cousins
				Acid- or base-catalyzed hydrolysis
				Dehydration
			Other reactions of carboxylic acids and derivatives
				Carbonic acid derivatives
				Decarboxylation
				Hunsdiecker reaction
				The Reformatsky reaction
		Taking a Look at Spectroscopy and Chemical Tests
			Identifying compounds through spectral data
			Using chemical tests
Part 4 Advanced Topics (Every Student’s Nightmare)
	Chapter 13 Amines and Friends
		Breaking Down the Structure and Nomenclature of Nitrogen Compounds
			Primary amines
			Secondary and tertiary amines
			Quaternary amines (quaternary ammonium salts)
			Heterocyclics
		Sizing Up the Physical Properties
		Understanding the Basicity of Nitrogen Compounds
		Synthesizing Nitrogen Compounds
			Nucleophilic substitution reactions
			Reduction preparations
				Nitro reductions
				Reductive amination
				Hofmann rearrangement (degradation)
		Seeing How Nitrogen Compounds React
			Reactions with nitrous acid
			Replacement reactions
				Sandmeyer reaction
				Replacement by iodide ion
				Schiemann reaction
				Formation of ethers and phenols
				Deamination
			Coupling reactions of diazonium salts
			Reactions with sulfonyl chlorides
			Exploring elimination reactions
				Hofmann elimination
				Cope elimination
		Mastering Multistep Synthesis
		Identifying Nitrogen Compounds with Analysis and Spectroscopy
	Chapter 14 Metals Muscling In: Organometallics
		Grignard Reagents: Grin and Bear It
			Preparation of Grignard reagents
			Reactions of Grignard reagents
				Basicity
				Nucleophilicity
		Organolithium Reagents
		Formation of Other Organometallics
		Putting It Together
	Chapter 15 More Reactions of Carbonyl Compounds
		Checking Out the Claisen Condensation and Its Variations
			Doing the two-step: Claisen condensation
			Circling around: Dieckmann condensation
			Doubling Up: Crossed Claisen condensation
			Other carbanions
		Exploring Acetoacetic Ester Synthesis
		Defining Malonic Ester Synthesis
		Working with Other Active Hydrogen Atoms
		Reacting with Knoevenagel Condensation
		Looking at Mannich Reactions
		Creating Enamines: Stork Enamine Synthesis
		Putting It All Together with Barbiturates
	Chapter 16 Living Large: Biomolecules
		Delving into Carbohydrate Complexities
			Introducing carbohydrates
				Mutarotation
				Glycoside formation
			Examining the many reactions of monosaccharides
				Oxidation of monosaccharides
				Reduction of monosaccharides
				Osazone formation
			Synthesizing and degrading monosaccharides
				Kiliani-Fischer synthesis
				Ruff degradation
			Meeting the (D-)aldose family
			Checking out a few disaccharides
				Sucrose
				Maltose
				Cellobiose
			Looking at some polysaccharides
				Starch
				Glycogen
				Cellulose
			Discovering nitrogen-containing sugars
		Lipids: Storing Energy Now So You Can Study Longer Later
			Pondering the properties of fats
			Soaping up with saponification
		Bulking Up on Amino Acids and Proteins
			Introducing amino acids
			Perusing the physical properties of amino acids
			Studying the synthesis of amino acids
				From α-halogenated acids
				From potassium phthalimide
				From amido malonic esters
				Strecker synthesis
				Reductive amination
				Resolution of (±) amino acids
Part 5 Pulling It All Together
	Chapter 17 Overview of Synthesis Strategies
		Working with One-Step Synthesis
		Tackling Multistep Synthesis
		Practicing Retrosynthetic and Synthetic Analysis
			Example 1
			Example 2
			Example 3
			Example 4
			Example 5
	Chapter 18 Roadmaps and Predicting Products
		Preparing with Roadmap Basics
		Practicing Roadmap Problems
			Problem one
			Solution one
			Problem two
			Solution two
			Problem three
			Solution three
		Predicting Products
Part 6 The Part of Tens
	Chapter 19 Ten Surefire Ways to Fail Organic Chemistry II
		Simply Read and Memorize Concepts
		Don’t Bother Working the Homework Problems and Exercises
		Don’t Buy a Model Kit
		Don’t Worry About Falling Behind
		Don’t Bother Learning Reactions
		If Your Textbook Confuses You, Don’t Bother with Additional Resources
		Don’t Bother Reading the Chapter before Attending Class
		Attend Class Only When You Feel Like It
		Don’t Bother Taking Notes — Just Listen (When You Aren’t Sleeping or Texting)
		Don’t Bother Asking Questions
	Chapter 20 More than Ten Ways to Increase Your Score on an Organic Chemistry Exam
		Don’t Cram the Night before a Test
		Try Doing the Problem Sets and Practice Tests Twice
		Study the Mistakes You Made on Previous Exams
		Know Precisely Where, Why, and How the Electrons Are Moving
		Relax and Get Enough Sleep before the Exam
		Think Before You Write
		Include Formal Charges in Your Structures When Appropriate
		Check That You Haven’t Lost Any Carbon Atoms
		Include E/Z, R/S, cis/trans Prefixes in Naming Organic Structures
		Think of Spectroscopy, Especially NMR, As a Puzzle
		Make Sure That Each Carbon Atom Has Four Bonds
	Chapter 21 Ten Simple Rules to Remember
		Carbon Has Four Bonds
		Positive Charges Attract Negative Charges
		Bulky Groups Lead to Steric Hindrance
		Like Dissolves Like
		Two Groups Must Be in Contact to React
		The Octet Rule
		The More Electronegative Atom Gets Its Electrons First
		If It’s Not C Or H, It’s Polar
		Hydrogen Bonding Occurs When H Is Bonded Directly to N, O, or F
		Markovnikov’s Rule: Them That Has Gets
Part 7 Appendixes
	Appendix A Named Reactions
	Appendix B A Few Great Online Resources
Index
EULA