Community College of Baltimore County Organic Chemistry 1
- Page ID
- 226991
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\(\newcommand{\avec}{\mathbf a}\) \(\newcommand{\bvec}{\mathbf b}\) \(\newcommand{\cvec}{\mathbf c}\) \(\newcommand{\dvec}{\mathbf d}\) \(\newcommand{\dtil}{\widetilde{\mathbf d}}\) \(\newcommand{\evec}{\mathbf e}\) \(\newcommand{\fvec}{\mathbf f}\) \(\newcommand{\nvec}{\mathbf n}\) \(\newcommand{\pvec}{\mathbf p}\) \(\newcommand{\qvec}{\mathbf q}\) \(\newcommand{\svec}{\mathbf s}\) \(\newcommand{\tvec}{\mathbf t}\) \(\newcommand{\uvec}{\mathbf u}\) \(\newcommand{\vvec}{\mathbf v}\) \(\newcommand{\wvec}{\mathbf w}\) \(\newcommand{\xvec}{\mathbf x}\) \(\newcommand{\yvec}{\mathbf y}\) \(\newcommand{\zvec}{\mathbf z}\) \(\newcommand{\rvec}{\mathbf r}\) \(\newcommand{\mvec}{\mathbf m}\) \(\newcommand{\zerovec}{\mathbf 0}\) \(\newcommand{\onevec}{\mathbf 1}\) \(\newcommand{\real}{\mathbb R}\) \(\newcommand{\twovec}[2]{\left[\begin{array}{r}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\ctwovec}[2]{\left[\begin{array}{c}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\threevec}[3]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\cthreevec}[3]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\fourvec}[4]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\cfourvec}[4]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\fivevec}[5]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\cfivevec}[5]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\mattwo}[4]{\left[\begin{array}{rr}#1 \amp #2 \\ #3 \amp #4 \\ \end{array}\right]}\) \(\newcommand{\laspan}[1]{\text{Span}\{#1\}}\) \(\newcommand{\bcal}{\cal B}\) \(\newcommand{\ccal}{\cal C}\) \(\newcommand{\scal}{\cal S}\) \(\newcommand{\wcal}{\cal W}\) \(\newcommand{\ecal}{\cal E}\) \(\newcommand{\coords}[2]{\left\{#1\right\}_{#2}}\) \(\newcommand{\gray}[1]{\color{gray}{#1}}\) \(\newcommand{\lgray}[1]{\color{lightgray}{#1}}\) \(\newcommand{\rank}{\operatorname{rank}}\) \(\newcommand{\row}{\text{Row}}\) \(\newcommand{\col}{\text{Col}}\) \(\renewcommand{\row}{\text{Row}}\) \(\newcommand{\nul}{\text{Nul}}\) \(\newcommand{\var}{\text{Var}}\) \(\newcommand{\corr}{\text{corr}}\) \(\newcommand{\len}[1]{\left|#1\right|}\) \(\newcommand{\bbar}{\overline{\bvec}}\) \(\newcommand{\bhat}{\widehat{\bvec}}\) \(\newcommand{\bperp}{\bvec^\perp}\) \(\newcommand{\xhat}{\widehat{\xvec}}\) \(\newcommand{\vhat}{\widehat{\vvec}}\) \(\newcommand{\uhat}{\widehat{\uvec}}\) \(\newcommand{\what}{\widehat{\wvec}}\) \(\newcommand{\Sighat}{\widehat{\Sigma}}\) \(\newcommand{\lt}{<}\) \(\newcommand{\gt}{>}\) \(\newcommand{\amp}{&}\) \(\definecolor{fillinmathshade}{gray}{0.9}\)- 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
- 3: Acids and Bases
- 3.1: An Introduction to Acids and Bases
- 3.2: pka and pH
- 3.3: Organic Acids and Bases
- 3.4: How to Predict the Outcome of an Acid-Base Reaction
- 3.5: How to Determine the Position of Equilibrium
- 3.6: How the Structure of an Acid Affects its pka Value
- 3.7: How pH Affects the Structure of an Organic Compound
- 3.8: Buffer Solutions
- 3.9: Lewis Acids and Bases
- 4: An Introduction to Organic Compounds- Nomenclature, Physical Properties, and Representation of Structure
- 4.1: How Alkyl Substituents Are Named
- 4.2: The Nomenclature of Alkanes
- 4.3: The Nomenclature of Cycloalkanes • Skeletal Structures
- 4.4: The Nomenclature of Alkyl Halides
- 4.5: The Structures of Alkyl Halides, Alcohols, Ethers, and Amines
- 4.6: The Physical Properties of Alkanes, Alkyl Halides, Alcohols, Ethers, and Amines
- 4.7: Rotation Occurs About Carbon-Carbon Single Bonds
- 4.8: Some Cycloalkanes Have Angle Strain
- 4.9: Conformers of Cyclohexane
- 4.10: Conformers of Monosubstituted Cyclohexanes
- 4.11: Conformers of Disubstituted Cyclohexanes
- 4.12: Fused Cyclohexane Rings
- 5: 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: How Enantiomers Can Be Separated
- 5.16: Nitrogen and Phosphorus Atoms Can Be Asymmetric Centers
- 6: Termodynamics, Kinetics, and Mechanisms
- 6.1: Chapter Objectives
- 6.2: Describing a Reaction - Bond Dissociation Energies
- 6.3: Describing a Reaction - Equilibria, Rates, and Energy Changes
- 6.4: Describing a Reaction - Energy Diagrams and Transition States
- 6.5: How Organic Reactions Occur - Mechanisms
- 6.6: Kinds of Organic Reactions
- 6.7: Radical Reactions
- 6.8: Polar Reactions
- 6.9: An Example of a Polar Reaction - Addition of HBr to Ethylene
- 6.10: Using Curved Arrows in Polar Reaction Mechanisms
- 6.11: Describing a Reaction- Intermediates
- 6.S: An Overview of Organic Reactions (Summary)
- 7: Reactions of Alkyl Halides- Nucleophilic Substitutions and Eliminations
- 7.1: Chapter Objectives
- 7.2: Introduction
- 7.3: The Discovery of Nucleophilic Substitution Reactions
- 7.4: The SN2 Reaction
- 7.5: Characteristics of the SN2 Reaction
- 7.6: The SN1 Reaction
- 7.7: Characteristics of the SN1 Reaction
- 7.8: Biological Substitution Reactions
- 7.9: Elimination Reactions- Zaitsev's Rule
- 7.10: The E2 Reaction and the Deuterium Isotope Effect
- 7.11: The E2 Reaction and Cyclohexane Conformation
- 7.12: The E1 and E1cB Reactions
- 7.13: Biological Elimination Reactions
- 7.14: A Summary of Reactivity - SN1, SN2, E1, E1cB, and E2
- 7.S: Reactions of Alkyl Halides - Nucleophilic Substitutions and Eliminations (Summary)
- 8: Alkenes- Structure and Reactivity
- This, the first of two chapters devoted to the chemistry of alkenes, describes how certain alkenes occur naturally, then shows the industrial importance of ethylene and propylene (the simplest members of the alkene family). The electronic structure of alkenes is reviewed, and their nomenclature discussed in detail.
- 8.1: Chapter Objectives
- 8.2: Introduction to Alkenes
- 8.3: Industrial Preparation and Use of Alkenes
- 8.4: Calculating Degree of Unsaturation
- 8.5: Naming Alkenes
- 8.6: Cis-Trans Isomerism in Alkenes
- 8.7: Sequence Rules - The E,Z Designation
- 8.8: Stability of Alkenes
- 8.9: Electrophilic Addition Reactions of Alkenes
- 8.10: Stereochemistry of Reactions- Regioselective, Stereoselective, and Stereospecific Reactions
- 8.11: The Stereochemistry of Electrophilic addition Reactions of Alkenes
- 8.12: Orientation of Electrophilic Additions - Markovnikov's Rule
- 8.13: Carbocation Structure and Stability
- 8.14: The Hammond Postulate
- 8.15: Evidence for the Mechanism of Electrophilic Additions - Carbocation Rearrangements
- 8.16: Structure and Reactivity (Summary)
- 8.S: Alkenes- Structure and Reactivity (Summary)
- 9: Alkynes
- Addition reactions not only dominate the chemistry of alkenes, they are also the major class of reaction for alkynes. An important difference between (terminal) alkynes and alkenes is the acidity of the former. We have now learned enough reactions that we can begin devising multi-step organic syntheses. The nomenclature of alkynes is explained in chapter 3.
- 9.1: Structure and Physical Properties
- 9.2: 10.2 Synthesis of Alkynes - Elimination Reactions of Dihalides
- 9.3: Reactions of Alkynes - Addition of HX and X₂
- 9.4: Hydration of Alkynes for Markovnikov Products
- 9.5: Hydration of Alkynes for Anti-Markovnikov Products
- 9.6: 10.6 Reduction of Alkynes
- 9.7: Oxidation of Alkynes
- 9.8: Acidity of Terminal Alkynes and Acetylide Ions
- 9.9: Synthesis of Larger Alkynes from Acetylides
- 9.10: An Introduction to Multiple Step Synthesis
- 9.11: Additional Exercises
- 9.12: Solutions to Additional Exercises
- 10: Radicals (Reactions of Alkanes)
- 10.1: Alkanes Are Unreactive Compounds
- 10.2: Chlorination and Bromination of Alkanes
- 10.3: Radical Stability Depends on the Number of Alkyl Groups Attached to the Carbon with the Unpaired Electron
- 10.4: The Distribution of Products Depends on Probability and Reactivity
- 10.5: The Reactivity-Selectivity Principle
- 10.6: The Addition of Radicals to an Alkene
- 10.7: The Stereochemistry of Radical Substitution and Addition Reactions
- 10.8: Radical Substitution of Benzylic and Allylic Hydrogens
- 10.9: Designing a Synthesis III- More Practice with Multistep Synthesis
- 11: Alcohols and Phenols
- In this unit, we examine the chemistry of the alcohol family of compounds. Alcohols can undergo a wide variety of reactions, and because of this reactivity and because they can be prepared in a number of different ways, alcohols occupy an important position in organic chemistry. The discussion begins with an outline of the nomenclature of alcohols and phenols. We review the physical properties of these compounds, and discuss methods used to obtain the lower members on an industrial scale.
- 11.1: Introduction
- 11.2: Naming Alcohols and Phenols
- 11.3: Properties of Alcohols and Phenols
- 11.4: Preparation of Alcohols- A Review
- 11.5: Alcohols from Carbonyl Compounds- Reduction
- 11.6: Alcohols from Carbonyl Compounds- Grignard Reagents
- 11.7: Reactions of Alcohols
- 11.8: Oxidation of Alcohols
- 11.9: Protection of Alcohols
- 11.10: Phenols and Their Uses
- 11.11: Reactions of Phenols
- 11.12: Spectroscopy of Alcohols and Phenols
- 11.S: Alcohols and Phenols (Summary)