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Chem 12A: Organic Chemistry

Chem 12A is the first semester in a year long course in organic chemistry designed for students majoring in chemistry and related disciplines. Hydrocarbons, alkyl halides, alcohols, ethers, and an introduction to aromatic hydrocarbons. Structure, bonding, stereochemistry, conformational analysis, nomenclature, and physical properties in relation to these particular groups of compounds. Emphasis on reactivity and reaction mechanisms.

Chemistry

Tác giả: Andy Wells
Nhà xuất bản: Chabot College
Nguồn: LibreTexts
Ngôn ngữ: EN
Danh mục: Khoa học cơ bản

Đọc trực tuyến Tải PDF (nguồn mở)

Mục lục· 171 mục

01: Introduction to Organic Chemistry- review of atoms and molecules
1.01: Introduction to Organic Chemistry
1.02: Structure of the Atom
1.03: The Electronic Structure of Atoms
1.04: Electron Configurations and Electronic Orbital Diagrams (Review)
1.05: Octet Rule - Ionic and Covalent Bonding (Review)
1.06: Lewis Structures and Formal Charges (Review)
1.07: Electron-Dot Model of Bonding - Lewis Structures
1.08: Common Bonding Patterns for Organic Chemistry
1.09: Hybridization and Molecular Shapes (Review)
1.10: Molecular Orbital (MO) Theory (Review)
02: Polarity Intermolecular Forces and Physical Properties of Molecules
2.01: Electronegativity and Bond Polarity (Review)
2.02: Intermolecular Forces (IMFs) - Review
2.03: Organic Functional Groups- H-bond donors and H-bond acceptors
2.04: Intermolecular Forces and Relative Boiling Points (bp)
2.05: Intermolecular Forces and Solubilities
03: Representations of Organic Molecules
3.01: Structural Formulas - Lewis Kekule Bond-line Condensed and Perspective
3.02: Isomerism Introduction
3.03: Resonance
3.04: Organic Functional Groups
04: Acids and Bases
4.01: Arrhenius Acids and Bases (Review)
4.02: Brnsted-Lowry Acids and Bases (Review)
4.03: Distinguishing between pH and pKa
4.04: Predicting Relative Acidity
4.05: Lewis Acids and Bases
05: Alkanes and Conformations
5.01: Hydrocarbons and the Homologous Series
5.02: Generic (Abbreviated) Structures (aka R Groups)
5.03: Overview of the IUPAC Naming Strategy
5.04: Alkanes
5.05: Uses and Sources of Alkanes
5.06: Cycloalkanes
5.07: Haloalkane - Classification and Nomenclature
5.08: Hydrocarbon Functional Groups
5.09: Physical Properties of Alkanes
5.10: Structure and Conformations of Alkanes
5.11: Conformations of Butane
5.12: Conformations of Higher Alkanes
5.13: Cycloalkanes and Ring Strain
5.14: Cyclohexane Conformations
5.15: Conformations of Monosubstituted Cyclohexanes
5.16: Cis-trans Isomerism in Cycloalkanes
5.17: Conformations of Disubstituted Cyclohexanes
5.18: Additional Exercises
5.19: Solutions to Additional Exercises
06: Stereoisomerism
6.01: Chirality
6.02: Fischer Projections to communicate Chirality
6.03: Absolute Configuration and the (R) and (S) System
6.04: Diastereomers - more than one chiral center
6.05: Meso Compounds
6.06: Isomerism Summary Diagram
6.07: Optical Activity and Racemic Mixtures
6.08: Resolution (Separation) of Enantiomers
07: Introduction to Organic Reactions
7.01: Describing a Reaction - Equilibrium and Free Energy Changes
7.02: Types of Organic Reactions
7.03: Reaction Mechanism Notation and Symbols
7.04: Polar Reactions- the Dance of the Nucleophile and Electrophile
7.05: Homolytic Cleavage and Bond Dissociation Energies
7.06: Reaction Energy Diagrams and Transition States
7.07: Reactive Intermediates - Carbocations
08: Nucleophilic Substitution Reactions
8.01: Alkyl Halides - Structure and Physical Properties
8.02: Reactions of Alkyl Halides- Substitution and Elimination
8.03: The S2 Reaction
8.04: Characteristics of the S2 Reaction
8.05: Stereochemistry of the SN2 Reaction
8.06: The S1 Reaction
8.07: Characteristics of the S1 Reaction
8.08: Rearrangements of the Carbocation and S1 Reactions
8.09: The Hammond Postulate and Transition States
8.10: Comparison of SN1 and SN2 Reactions
8.11: Biological Substitution Reactions
09: Elimination Reactions
9.01: Reactions of Alkyl Halides- Substitution and Elimination
9.02: Characteristics of the E2 Reaction
9.03: Zaitsev's Rule
9.04: Characteristics of the E1 Reaction
9.05: E2 Regiochemistry and Cyclohexane Conformations
9.06: The E2 Reaction and the Deuterium Isotope Effect
9.07: Comparison of E1 and E2 Reactions
9.08: Comparing Substitution and Elimination Reactions
9.09: Biological Elimination Reactions
9.10: Additional Exercises
9.11: Solutions to Additional Exercises
10: Properties and Reactions of Alkenes
10.01: Alkene Structure
10.02: Physical Properties and Important Common Names
10.03: The Alkene Double Bond and Stereoisomerism
10.04: Degrees of Unsaturation
10.05: The E Z System (when cis trans does not work)
10.06: Stability of Alkenes
10.07: Alkene Synthesis by Elimination of Alkyl Halides
10.08: Alkene Synthesis by Dehydration of Alcohols
10.09: Additional Exercises. Part 1
10.10: Solutions to Additional Exercises Part 1
10.11: Electrophilic Addition Reactions (EARs)
10.12: Addition of Hydrogen Halides to Symmetrical Alkenes
10.13: Alkene Asymmetry and Markovnikov's Rule
10.14: Hydration- Acid Catalyzed Addition of Water
10.15: Hydration- Oxymercuration-Demercuration
10.16: Hydration - Hydroboration-Oxidation
10.17: Stereochemistry of Reactions - Hydration of Achiral Alkenes
10.18: Stereochemistry of Reactions - Hydration of Chiral Alkenes
10.19: Addition of Halogens
10.20: Formation of Halohydrins
10.21: Reduction of Alkenes - Catalytic Hydrogenation
10.22: Oxidation of Alkenes - Epoxidation
10.23: Dihydroxylation of Alkenes
10.24: Oxidative Cleavage of Alkenes
10.25: Additional Exercises Part 2
10.26: Solutions to Additional Exercises Part 2
11: Properties and Reactions of Alkynes
11.01: Structure and Physical Properties
11.02: 10.2 Synthesis of Alkynes - Elimination Reactions of Dihalides
11.03: Reactions of Alkynes - Addition of HX and X
11.04: Hydration of Alkynes for Markovnikov Products
11.05: Hydration of Alkynes for Anti-Markovnikov Products
11.06: 10.6 Reduction of Alkynes
11.07: Oxidation of Alkynes
11.08: Acidity of Terminal Alkynes and Acetylide Ions
11.09: Synthesis of Larger Alkynes from Acetylides
11.10: An Introduction to Multiple Step Synthesis
11.11: Additional Exercises
11.12: Solutions to Additional Exercises
12: Free Radical Reactions
12.01: Reactive Intermediates - Radicals
12.02: The Free-Radical Halogenation of Alkanes
12.03: Radical-Chain Addition Reactions to Alkenes
13: Properties and Reactions of Alcohols
13.01: Introduction to Structure and Synthesis of Alcohols
13.02: Classification of Alcohols
13.03: Physical Properties of Alcohols
13.04: Spectroscopy of Alcohols
13.05: Synthesis of Alcohols - Review
13.06: Acidity of Alcohols and Phenols
13.07: Reduction of the Carbonyl Group - Synthesis of 1 and 2 Alcohols
13.08: Organometallic Reagents
13.09: Organometallic Reagents in Alcohol Synthesis
13.10: Additional Exercises Part 1
13.11: Solutions to Additional Exercises Part 1
13.12: Reactions of Alcohols with Hydrohalic Acids
13.13: Reactions with Phosphorus Halides and Thionyl Chloride
13.14: Dehydration Reactions of Alcohols
13.15: Oxidation States of Alcohols and Related Functional Groups
13.16: Oxidation Reactions of Alcohols
13.17: Protection of Alcohols
13.18: Additional Exercises Part 2
13.19: Solutions to Additional Exercises Part 2
14: Infrared Spectroscopy and Mass Spectrometry
14.01: The Electromagnetic Spectrum and Spectroscopy
14.02: Infrared (IR) Spectroscopy
14.03: IR-Active and IR-Inactive Vibrations
14.04: Interpretting IR Spectra
14.05: Infrared Spectra of Some Common Functional Groups
14.06: Summary and Tips to Distinguish between Carbonyl Functional Groups
15: Nuclear Magnetic Resonance Spectroscopy
15.01: Theory of Nuclear Magnetic Resonance (NMR)
15.02: NMR Spectra - an introduction and overview
15.03: Chemical Shifts and Shielding
15.04: H NMR Spectroscopy and Proton Equivalence
15.05: Functional Groups and Chemical Shifts in H NMR Spectroscopy
15.06: Integration of H NMR Absorptions- Proton Counting
15.07: Spin-Spin Splitting in H NMR Spectra
15.08: More Complex Spin-Spin Splitting Patterns
15.09: Uses of H NMR Spectroscopy
15.10: Sample NMR Spectra