Map: Essential Organic Chemistry (Bruice)
- Page ID
- 17843
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\(\newcommand{\avec}{\mathbf a}\) \(\newcommand{\bvec}{\mathbf b}\) \(\newcommand{\cvec}{\mathbf c}\) \(\newcommand{\dvec}{\mathbf d}\) \(\newcommand{\dtil}{\widetilde{\mathbf d}}\) \(\newcommand{\evec}{\mathbf e}\) \(\newcommand{\fvec}{\mathbf f}\) \(\newcommand{\nvec}{\mathbf n}\) \(\newcommand{\pvec}{\mathbf p}\) \(\newcommand{\qvec}{\mathbf q}\) \(\newcommand{\svec}{\mathbf s}\) \(\newcommand{\tvec}{\mathbf t}\) \(\newcommand{\uvec}{\mathbf u}\) \(\newcommand{\vvec}{\mathbf v}\) \(\newcommand{\wvec}{\mathbf w}\) \(\newcommand{\xvec}{\mathbf x}\) \(\newcommand{\yvec}{\mathbf y}\) \(\newcommand{\zvec}{\mathbf z}\) \(\newcommand{\rvec}{\mathbf r}\) \(\newcommand{\mvec}{\mathbf m}\) \(\newcommand{\zerovec}{\mathbf 0}\) \(\newcommand{\onevec}{\mathbf 1}\) \(\newcommand{\real}{\mathbb R}\) \(\newcommand{\twovec}[2]{\left[\begin{array}{r}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\ctwovec}[2]{\left[\begin{array}{c}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\threevec}[3]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\cthreevec}[3]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\fourvec}[4]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\cfourvec}[4]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\fivevec}[5]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\cfivevec}[5]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\mattwo}[4]{\left[\begin{array}{rr}#1 \amp #2 \\ #3 \amp #4 \\ \end{array}\right]}\) \(\newcommand{\laspan}[1]{\text{Span}\{#1\}}\) \(\newcommand{\bcal}{\cal B}\) \(\newcommand{\ccal}{\cal C}\) \(\newcommand{\scal}{\cal S}\) \(\newcommand{\wcal}{\cal W}\) \(\newcommand{\ecal}{\cal E}\) \(\newcommand{\coords}[2]{\left\{#1\right\}_{#2}}\) \(\newcommand{\gray}[1]{\color{gray}{#1}}\) \(\newcommand{\lgray}[1]{\color{lightgray}{#1}}\) \(\newcommand{\rank}{\operatorname{rank}}\) \(\newcommand{\row}{\text{Row}}\) \(\newcommand{\col}{\text{Col}}\) \(\renewcommand{\row}{\text{Row}}\) \(\newcommand{\nul}{\text{Nul}}\) \(\newcommand{\var}{\text{Var}}\) \(\newcommand{\corr}{\text{corr}}\) \(\newcommand{\len}[1]{\left|#1\right|}\) \(\newcommand{\bbar}{\overline{\bvec}}\) \(\newcommand{\bhat}{\widehat{\bvec}}\) \(\newcommand{\bperp}{\bvec^\perp}\) \(\newcommand{\xhat}{\widehat{\xvec}}\) \(\newcommand{\vhat}{\widehat{\vvec}}\) \(\newcommand{\uhat}{\widehat{\uvec}}\) \(\newcommand{\what}{\widehat{\wvec}}\) \(\newcommand{\Sighat}{\widehat{\Sigma}}\) \(\newcommand{\lt}{<}\) \(\newcommand{\gt}{>}\) \(\newcommand{\amp}{&}\) \(\definecolor{fillinmathshade}{gray}{0.9}\)This is a TextMap of Bruice's "Essential Organic Chemistry" textbook. It is not a copy of the original textbook, but is mapped to content on the ChemWiki to recreate the utility of the textbook in the same organization.
- 1: Electronic Structure and Covalent Bonding
- 1.1: The Structure of an Atom
- 1.2: How Electrons in an Atom are Distributed
- 1.3: Ionic and Covalent Bonds
- 1.4: How the Structure of a Compound is Represented
- 1.5: Atomic Orbitals
- 1.6: How atoms form Covalent Bonds
- 1.7: How Single Bonds Are Formed in Organic Compounds
- 1.8: How a Double Bond is Formed: The Bonds in Ethene
- 1.9: How a Triple Bond is Formed: The Bonds in Ethyne
- 1.10: Bonding in the Methyl Cation, the Methyl Radical, and the Methyl Anion
- 1.11: The Bonds in Water
- 1.12: The Bonds in Ammonia and in the Ammonium Ion
- 1.13: The Bond in a Hydrogen Halide
- 1.14: Summary: Hybridization, Bond Lengths, Bond Strengths, and Bond Angles
- 1.15: The Dipole Moments of Molecules
- 1.16: An Introduction to Acids and Bases
- 1.17: pka and pH
- 1.18 Organic Acids and Bases
- 1.19: How to Predict the Outcome of an Acid-Base Reaction
- 1.20: How to Determine the Position of Equilibrium
- 1.21: How the Structure of an Acid Affects its pka Value
- 1.22: How Substituents Affect the Strength of an Acid
- 1.23: An Introduction to Delocalized Electrons
- 1.24: A Summary of the Factors that Determine Acid Strength
- 1.25: How pH Affects the Structure of an Organic Compound
- 1.26: Buffer Solutions
- 1.27: Lewis Acids and Bases
- 2: Acids and Bases
- 2.1: An Introduction to Acids and Bases
- 2.2: pka and pH
- 2.3: Organic Acids and Bases
- 2.4: How to Predict the Outcome of an Acid-Base Reaction
- 2.5: How to Determine the Position of Equilibrium
- 2.6: How the Structure of an Acid Affects its pka Value
- 2.7: How pH Affects the Structure of an Organic Compound
- 2.8: Buffer Solutions
- 2.9: Lewis Acids and Bases
- 3: An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Representation of Structure
- 3.1: How Alkyl Substituents Are Named
- 3.2: The Nomenclature of Alkanes
- 3.3: The Nomenclature of Cycloalkanes • Skeletal Structures
- 3.4: The Nomenclature of Alkyl Halides
- 3.6: The Structures of Alkyl Halides, Alcohols, Ethers, and Amines
- 3.7: The Physical Properties of Alkanes, Alkyl Halides, Alcohols, Ethers, and Amines
- 3.8: Rotation Occurs About Carbon-Carbon Single Bonds
- 3.9: Some Cycloalkanes Have Angle Strain
- 3.10: Conformers of Cyclohexane
- 3.11: Conformers of Monosubstituted Cyclohexanes
- 3.12: Conformers of Disubstituted Cyclohexanes
- 3.13: Fused Cyclohexane Rings
- 4: Alkenes: Structure, Nomenclature, and an Introduction to Reactivity
- 4.1: Molecular Formulas and the Degree of Unsaturation
- 4.2: The Nomenclature of Alkenes
- 4.3: The Structures of Alkenes
- 4.4: Alkenes Can Have Cis and Trans Isomers
- 4.5: Naming Alkenes Using the E,Z System
- 4.7: How Alkenes React (Curved Arrows Show the Flow of Electrons)
- 4.8: A Reaction Coordinate Diagram Describes the Energy Changes That Take Place During a Reaction
- 5: The Reactions of Alkenes and Alkynes: An Introduction to Multistep Synthesis
- 5.1: The Addition of a Hydrogen Halide to an Alkene
- 5.2: Carbocation Stability Depends on the Number of Alkyl Groups Attached to the Positively Charged Carbon
- 5.4: Electrophilic Addition Reactions Are Regioselective
- 5.4: The Addition of Water to an Alkene
- 5.5: The Addition of an Alcohol to an Alkene
- 5.7: The Nomenclature of Alkynes
- 5.8: The Structure of Alkynes
- 5.9: The Physical Properties of Unsaturated Hydrocarbons
- 5.10: The Addition of Hydrogen Halides and Addition of Halogens to an Alkyne
- 5.12: The Addition of Hydrogen to Alkenes and Alkynes
- 5.13: A Hydrogen Bonded to an sp Carbon is “Acidic”
- 5.14: Synthesis Using Acetylide Ions
- 5.15: An Introduction to Multistep Synthesis
- 6: Isomers and Stereochemistry
- 5.1: Cis-Trans Isomers Result from Restricted Rotation
- 5.2: A Chiral Object Has a Nonsuperimposable Mirror Image
- 5.3: An Asymmetric Center Is a Cause of Chirality in a Molecule
- 5.4: Isomers with One Asymmetric Center
- 5.5: Asymmetric Centers and Stereocenters
- 5.6: How to Draw Enantiomers
- 5.7: Naming Enantiomers by the R,S System
- 5.8: Chiral Compounds Are Optically Active
- 5.9: How Specific Rotation is Measured
- 5.10: Enantiomeric Excess
- 5.11: Isomers with More than One Asymmetric Center
- 5.12: Meso Compounds Have Asymmetric Centers but Are Optically Inactive
- 5.13: How to Name Isomers with More than One Asymmetric Center
- 5.14: Reactions of Compounds that Contain an Asymmetric Center
- 5.15: Using Reactions that Do Not Break Bonds to an Asymmetric Center to Determine Relative Configurations
- 5.16: How Enantiomers Can Be Separated
- 5.17: Nitrogen and Phosphorus Atoms Can Be Asymmetric Centers
- 5.18: Stereochemistry of Reactions: Regioselective, Stereoselective, and Stereospecific Reactions
- 5.19: The Stereochemistry of Electrophilic addition Reactions of Alkenes
- 5.20: The Stereochemistry of Enzyme-Catalyzed Reactions
- 5.21: Enantiomers Can Be Distinguished by Biological Molecules
- 7: Delocalized Electrons and Their Effect on Stability, Reactivity, and pKa (Ultraviolet and Visible Spectroscopy)
- 7.1: Delocalized Electrons Explain Benzene’s Structure
- 7.2: The Bonding in Benzene
- 7.3: Resonance Contributors and the Resonance Hybrid
- 7.4: How to Draw Resonance Contributors
- 7.5: The Predicted Stabilities of Resonance Contributors
- 7.6: Delocalized Energy Is the Additional Stability Delocalized Electrons Give to a Compound
- 7.7: Examples That Show How Delocalized Electrons Affect Stability
- 7.8: A Molecular Orbital Description of Stability
- 7.9: How Delocalized Electrons Affect pKa Values
- 7.10: Delocalized Electrons Can Affect the Product of a Reaction
- 7.11: Thermodynamic Versus Kinetic Control of Reactions
- 7.12: The Diels-Adler Reaction Is a 1,4-Addition Reaction
- 8: Aromaticity: Reactions of Benzene and Substituted Benzenes
- 8.1: The Two Criteria for Aromaticity
- 8.2: Applying the Criteria for Aromaticity
- 8.3: Aromatic Heterocyclic Compounds
- 8.4: The Nomenclature of Monosubstituted Benzenes
- 8.5: How Benzene Reacts
- 8.6: The General Mechanism for Electrophilic Aromatic Substitution Reactions
- 8.7: Halogenation of Benzene
- 8.8: Nitration of Benzene
- 8.9: Sulfonation of Benzene
- 8.10: The Friedel-Crafts Acylation of Benzene
- 8.11: The Friedel-Crafts Alkylation of Benzene
- 8.13: The Nomenclature of Disubstituted and Polysubstituted Benzenes
- 8.14: The Effect of Substituents on Reactivity
- 8.15: The Effect of Substituents on Orientation
- 8.17: The Effect of Substituents on pKa
- 9: Substitution and Elimination Reactions of Alkyl Halides
- 9.1: How Alkyl Halides React
- 9.2: The Mechanism For an \(S_N2\) Reaction
- 9.3: Factors That Affect \(S_N2\) Reactions
- 9.4: The Mechanism for an \(S_N1\) Reaction
- 9.5: Factors That Affect \(S_N1\) Reactions
- 9.6: Comparing the \(S_N2\) and \(S_N1\) Reactions of Alkyl Halides
- 9.7: Elimination Reaction of Alkyl Halides
- 9.8: Products of Elimination Reactions
- 9.9: Comparing the E2 and E1 Reactions of Alkyl Halides
- 9.10: Does an Alkyl Halide Undergo SN2, E2 Reactions or SN1 Reactions?
- 9.11: Does an Alkyl Halide Undergo SN2/E2 Reactions or SN1/E1 Reactions?
- 9.12: Solvent Effects
- 9.13: Using Substitution Reactions to Synthesize Organic Compounds
- 9.14: Biological Methylating Reagents
- 10: Reactions of Alcohols, Amines, Ethers, and Epoxides
- 10.1: Nomenclature of Alcohols
- 10.2: Substitution Reactions of Alcohols
- 10.3: Elimination Reactions of Alcohols: Dehydration
- 10.4: Oxidation of Alcohols
- 10.5: Amines Do Not Undergo Substitution or Elimination Reactions
- 10.6: Nomenclature of Ethers
- 10.7: Nucleophilic Substitution Reactions of Ethers
- 10.8: Nucleophilic Substitution Reactions of Epoxides
- 10.9: Using Carbocation Stability to Determine the Carcinogenicity of an Arene Oxide
- 11: Carbonyl Compounds I: Reactions of Carboxylic Acids and Carboxylic Derivatives
- 11.1: The Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives
- 11.2: The Structures of Carboxylic Acids and Carboxylic Acid Derivatives
- 11.3: The Physical Properties of Carbonyl Compounds
- 11.4: Carboxylic Acids and Carboxylic Acid Derivatives found in Nature
- 11.5: How Carboxylic Acids and Carboxylic Acids Compounds React
- 11.6: Relative Reactivities of Carboxylic Acids and Carboxylic Acid Derivatives
- 11.7: Reactions of Acyl Halides
- 11.8: Reactions of Esters
- 11.9: Acid-Catalyzed Ester Hydrolysis
- 11.10: Soaps, Detergents, and Micelles
- 11.11: Reactions of Carboxylic Acids
- 11.12: Reactions of Amides
- 11.13: Acid-Catalyzed Amide Hydrolysis
- 11.14: The Synthesis of Carboxylic Acid Derivatives
- 11.15: Nitriles
- 12: Carbonyl Compounds II: Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives
- 12.1: The Nomenclature of Aldehydes and Ketones
- 12.2: The Relative Reactivities of Carbonyl Compounds
- 12.3: How Aldehydes and Ketones React
- 12.4: Gringard Reagents
- 12.6: Reactions of Carbonyl Compounds with Hydride Ion
- 12.7: Reactions of Aldehydes and Ketones with Amines
- 12.8: Reactions of Aldehydes and Ketones with Water
- 12.9: Reactions of Aldehydes and Ketones with Alcohols
- 12.10: Nucleophilic Addition to α, β- Unsaturated Carboxylic Acid Derivatives
- 12.10: Nucleophilic Addition to α, β- Unsaturated Carbonyl Compounds
- 18.11 Protecting Groups
- 18.12 Addition of Sulfur Nucleophiles
- 18.13 The Wittig Reaction Forms an Alkene
- 18.14 Stereochemistry of Nucleophilic Addition Reactions: Re and Si Faces
- 18.15 Designing a Synthesis VI: Disconnections, Synthons, and Synthetic Equivalents
- 18.18 Enzyme-Catalyzed Additions to α, β- Unsaturated Carbonyl Compounds
- 13: Carbonyl Compounds III: Reactions at the α- Carbon
- 19.10 Alkylation and Acylation of the α-Carbon Using an Enamine Intermediate
- 19.11 Alkylation of the β-Carbon: The Michael Reaction
- 19.12 An Aldol Addition Forms β-Hydroxaldehydes or β-Hydroxyketones
- 19.13 Dehydration of Aldol Addition Products Form α, β-Unsaturated Aldehydes and Ketones
- 19.14 The Crossed Aldol Addition
- 19.15 A Claisen Condensation Forms a β-Keto Ester
- 19.16 Other Crossen Condensations
- 19.17 Intramolecular Condensation and Addition Reactions
- 19.18 The Robinson Annulation
- 19.19 Carboxylic Acids with a Carbonyl Group at the 3-Position can be Decarboxylated
- 19.1 The Acidity of an α- Hydrogen
- 19.20 The Malonic Ester Synthesis: A Way to Synthesize a Carboxylic Acid
- 19.21 The Acetoacetic Ester Synthesis: A Way to Synthesize a Methyl Ketone
- 19.22 Designing a Synthesis VII: Making New Carbon-Carbon Bonds
- 19.23 Reactions at the α-Carbon in Biological Systems
- 19.2 Keto-Enol Tautomers
- 19.3 Keto-Enol Interconversion
- 19.4 How Enolate Ions and Enols React
- 19.5 Halogenation of the α- Carbon and Aldehydes and Ketones
- 19.6 Halogenation of the α- Carbon of Carboxylic Acids: The Hell-Volhard-Zelinski Reaction
- 19.7 α- Halogenated Carbonyl Compounds Are Useful in Synthesis
- 19.8 Using LDA to Form an Enolate Ion
- 19.9 Alkylating the α-Carbon of Carbonyl Compounds
- 15: The Organic Chemistry of Carbohydrates
- 22.1: Classification of Carbohydrates
- 22.2: The D and L Notation
- 22.3: The Configurations of Aldoses
- 22.4: The Configurations of Ketoses
- 22.5: The Reactions of Monosaccharides in Basic Solutions
- 22.6: The Oxidation-Reduction Reactions of Monosaccharides
- 22.7: Monosaccharides form Crystalline Osazones
- 22.8: Lengthening the Chain: The Kiliani-Fischer Synthesis
- 22.9: Shortening the Chain: The Wohl Degradation
- 22.10 The Stereochemistry of Glucose: The Fischer Proof
- 22.11 Monosaccharides Form Cyclic Hemiacetals
- 22.12: Glucose is the Most Stable Aldohexose
- 22.13 Formation of Glycosides
- 22.14 The Anomeric Effect
- 22.15 Reducing and Nonreducing Sugars
- 22.16 Disaccharides
- 22.17 Polysaccharides
- 22.18 Some Naturally Occurring Products Derived from Carbohydrates
- 22.19 Carbohydrates on Cell Surfaces
- 22.20 Synthetic Sweeteners
- 16: The Organic Chemistry of Amino Acids, Peptides, and Proteins
- 16.1: Classification and Nomenclature of Amino Acids
- 16.2: The Configuration of the Amino Acids
- 16.3: The Acid-Base Properties of Amino Acids
- 16.4: The Isoelectric Point
- 16.5: Separating Amino Acids
- 16.6: Peptide Bond and Disulfide Bonds
- 16.7: The Strategy of Peptide Bond Synthesis: N-Protection and C-Activation
- 16.8: An Introduction to Protein Structure
- 16.9: Determining the Primary Structure of a Polypeptide or Protein
- 16.10 The Secondary Structure of Proteins
- 16.11: The Tertiary Structure of Proteins
- 16.12: The Quaternary Structure of Proteins
- 16.13: Protein Denaturation
- 20: The Chemistry of Nucleic Acids
- 20.1: Nucleosides and Nucleotides
- 20.2: Nucleic Acids Are Composed of Nucleotide Subunits
- 20.3: Why DNA Does Not Have A 2’- OH Group
- 20.4: The Biosynthesis of DNA is Called Replication
- 20.5: DNA and Heredity
- 20.6: The Biosynthesis of RNA is Called Transcription
- 20.7: There Are Three Kinds of RNA
- 20.8: The Biosynthesis of Proteins Is Called Translation
- 20.9: Why DNA Contains Thymine Instead of Uracil
- 20.10: How the Base Sequence of DNA Is Determined
- 20.11: The Polymerase Chain Reaction (PCR)
- 20.12: Genetic Engineering