1: Chapters
- Page ID
- 20968
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\(\newcommand{\avec}{\mathbf a}\) \(\newcommand{\bvec}{\mathbf b}\) \(\newcommand{\cvec}{\mathbf c}\) \(\newcommand{\dvec}{\mathbf d}\) \(\newcommand{\dtil}{\widetilde{\mathbf d}}\) \(\newcommand{\evec}{\mathbf e}\) \(\newcommand{\fvec}{\mathbf f}\) \(\newcommand{\nvec}{\mathbf n}\) \(\newcommand{\pvec}{\mathbf p}\) \(\newcommand{\qvec}{\mathbf q}\) \(\newcommand{\svec}{\mathbf s}\) \(\newcommand{\tvec}{\mathbf t}\) \(\newcommand{\uvec}{\mathbf u}\) \(\newcommand{\vvec}{\mathbf v}\) \(\newcommand{\wvec}{\mathbf w}\) \(\newcommand{\xvec}{\mathbf x}\) \(\newcommand{\yvec}{\mathbf y}\) \(\newcommand{\zvec}{\mathbf z}\) \(\newcommand{\rvec}{\mathbf r}\) \(\newcommand{\mvec}{\mathbf m}\) \(\newcommand{\zerovec}{\mathbf 0}\) \(\newcommand{\onevec}{\mathbf 1}\) \(\newcommand{\real}{\mathbb R}\) \(\newcommand{\twovec}[2]{\left[\begin{array}{r}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\ctwovec}[2]{\left[\begin{array}{c}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\threevec}[3]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\cthreevec}[3]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\fourvec}[4]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\cfourvec}[4]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\fivevec}[5]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\cfivevec}[5]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\mattwo}[4]{\left[\begin{array}{rr}#1 \amp #2 \\ #3 \amp #4 \\ \end{array}\right]}\) \(\newcommand{\laspan}[1]{\text{Span}\{#1\}}\) \(\newcommand{\bcal}{\cal B}\) \(\newcommand{\ccal}{\cal C}\) \(\newcommand{\scal}{\cal S}\) \(\newcommand{\wcal}{\cal W}\) \(\newcommand{\ecal}{\cal E}\) \(\newcommand{\coords}[2]{\left\{#1\right\}_{#2}}\) \(\newcommand{\gray}[1]{\color{gray}{#1}}\) \(\newcommand{\lgray}[1]{\color{lightgray}{#1}}\) \(\newcommand{\rank}{\operatorname{rank}}\) \(\newcommand{\row}{\text{Row}}\) \(\newcommand{\col}{\text{Col}}\) \(\renewcommand{\row}{\text{Row}}\) \(\newcommand{\nul}{\text{Nul}}\) \(\newcommand{\var}{\text{Var}}\) \(\newcommand{\corr}{\text{corr}}\) \(\newcommand{\len}[1]{\left|#1\right|}\) \(\newcommand{\bbar}{\overline{\bvec}}\) \(\newcommand{\bhat}{\widehat{\bvec}}\) \(\newcommand{\bperp}{\bvec^\perp}\) \(\newcommand{\xhat}{\widehat{\xvec}}\) \(\newcommand{\vhat}{\widehat{\vvec}}\) \(\newcommand{\uhat}{\widehat{\uvec}}\) \(\newcommand{\what}{\widehat{\wvec}}\) \(\newcommand{\Sighat}{\widehat{\Sigma}}\) \(\newcommand{\lt}{<}\) \(\newcommand{\gt}{>}\) \(\newcommand{\amp}{&}\) \(\definecolor{fillinmathshade}{gray}{0.9}\) UC Davis CHE 8A: Organic Chemistry | ||
- 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: 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
- 3.5: The Structures of Alkyl Halides, Alcohols, Ethers, and Amines
- 3.6: The Physical Properties of Alkanes, Alkyl Halides, Alcohols, Ethers, and Amines
- 3.7: Rotation Occurs About Carbon-Carbon Single Bonds
- 3.8: Some Cycloalkanes Have Angle Strain
- 3.9: Conformers of Cyclohexane
- 3.10: Conformers of Monosubstituted Cyclohexanes
- 3.11: Conformers of Disubstituted Cyclohexanes
- 3.12: 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
- 4.6: How Alkenes React (Curved Arrows Show the Flow of Electrons)
- 4.7: 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
- 5.3: Electrophilic Addition Reactions Are Regioselective
- 5.4: The Addition of Water to an Alkene
- 5.5: The Addition of an Alcohol to an Alkene
- 5.6: The Nomenclature of Alkynes
- 5.7: The Structure of Alkynes
- 5.8: The Physical Properties of Unsaturated Hydrocarbons
- 5.9: The Addition of Hydrogen Halides and Addition of Halogens to an Alkyne
- 5.10: The Addition of Hydrogen to Alkenes and Alkynes
- 5.11: A Hydrogen Bonded to an sp Carbon is “Acidic”
- 5.12: Synthesis Using Acetylide Ions
- 5.13: An Introduction to Multistep Synthesis
- 6: Isomers and Stereochemistry
- 6.1: Cis-Trans Isomers Result from Restricted Rotation
- 6.2: A Chiral Object Has a Nonsuperimposable Mirror Image
- 6.3: An Asymmetric Center Is a Cause of Chirality in a Molecule
- 6.4: Isomers with One Asymmetric Center
- 6.5: Asymmetric Centers and Stereocenters
- 6.6: How to Draw Enantiomers
- 6.7: Naming Enantiomers by the R,S System
- 6.8: Chiral Compounds Are Optically Active
- 6.9: How Specific Rotation is Measured
- 6.10: Enantiomeric Excess
- 6.11: Isomers with More than One Asymmetric Center
- 6.12: Meso Compounds Have Asymmetric Centers but Are Optically Inactive
- 6.13: How to Name Isomers with More than One Asymmetric Center
- 6.14: Reactions of Compounds that Contain an Asymmetric Center
- 6.15: Using Reactions that Do Not Break Bonds to an Asymmetric Center to Determine Relative Configurations
- 6.16: How Enantiomers Can Be Separated
- 6.17: Nitrogen and Phosphorus Atoms Can Be Asymmetric Centers
- 6.18: Stereochemistry of Reactions- Regioselective, Stereoselective, and Stereospecific Reactions
- 6.19: The Stereochemistry of Electrophilic addition Reactions of Alkenes
- 6.20: The Stereochemistry of Enzyme-Catalyzed Reactions
- 6.21: 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
- 8.12: The Nomenclature of Disubstituted and Polysubstituted Benzenes
- 8.13: The Effect of Substituents on Reactivity
- 8.14: The Effect of Substituents on Orientation
- 8.15: 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
- 9.12: Solvent Effects
- 9.13: Using Substitution Reactions to Synthesize Organic Compounds
- 9.14: Biological Methylating Reagents
- 10: The Chemistry of Nucleic Acids
- 10.1: Nucleosides and Nucleotides
- 10.2: Nucleic Acids Are Composed of Nucleotide Subunits
- 10.3: Why DNA Does Not Have A 2’- OH Group
- 10.4: The Biosynthesis of DNA is Called Replication
- 10.5: DNA and Heredity
- 10.6: The Biosynthesis of RNA is Called Transcription
- 10.7: There Are Three Kinds of RNA
- 10.8: The Biosynthesis of Proteins Is Called Translation
- 10.9: Why DNA Contains Thymine Instead of Uracil
- 10.10: How the Base Sequence of DNA Is Determined
- 10.11: The Polymerase Chain Reaction (PCR)
- 10.12: Genetic Engineering