Organic Chemistry II For Dummies, 2nd Edition
- Length: 384 pages
- Edition: 2
- Language: English
- Publisher: For Dummies
- Publication Date: 2023-02-01
- ISBN-10: 111998517X
- ISBN-13: 9781119985174
- Sales Rank: #3074722 (See Top 100 Books)
With Dummies at your side, you can conquer O-chem
Organic chemistry is, well, tough. With Organic Chemistry II For Dummies, you can (and will!) succeed at one of the most difficult college courses you’ll encounter. We make the subject less daunting in the second semester, with a helpful review of what you learned in Organic Chemistry I, clear descriptions of organic reactions, hints for working with synthesis and roadmaps, and beyond. You’ll love the straightforward, effective way we explain advanced O-chem material. This updated edition is packed with new practice problems, fresh examples, and updated exercises to help you learn quickly. Observe from a macroscopic and microscopic view, understand the properties of organic compounds, get an overview of carbonyl group basics, and everything else you’ll need to pass the class. Organic Chemistry II For Dummies is packed with tips to help you boost your exam scores, stay on track with assignments, and navigate advanced topics with confidence.
- Brush up on concepts from Organic Chemistry I
- Understand the properties of organic compounds
- Access exercises and practice questions to hone your knowledge
- Improve your grade in the second semester of Organic Chemistry
Organic Chemistry II For Dummies is for students who want a reference that explains concepts and terms more simply. It’s also a perfect refresher O-chem veterans preparing for the MCAT.
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 Example Example Example Example 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
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