ORGANIC CHEMISTRY I REVIEW FOR FINAL EXAM

Dr. Gholam Pahlavan

Chapter 1: Structure and Bonding -you should know;
1. Atomic Structure- Orbitals, Electron Configurations
2. Valence Bond Theory and Molecular Orbital Theory
3. Hybridization: sp3 Orbitals and the Structure of Methane, sp2 Orbitals and the Structure of
Ethylene, sp Orbitals and the Structure of Acetylene, and Hybridization of Other Atoms:
Nitrogen and Oxygen
Chapter 2: You should know;
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Polar Covalent Bonds and Electronegativity

Resonances and how to draw resonance forms
Acid-base strength
Curved-arrow formalism
Polar Covalent Bonds , Dipole Moment, and Formal Charges
Acids and Bases: The BrnstedLowry, and Lewis Definitions, Acid and Base Strength
Predicting AcidBase Reactions from pKa Values
Drawing Chemical Structures (Lewis Dot Structure)

Chapter 3: Organic Compounds: Alkanes and Cycloalkanes- you should know;

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Functional Groups
Structure and Bonding
Alkyl Groups
Naming Alkanes, Properties of Alkanes
Cycloalkanes, Naming Cycloalkanes, Cis-Trans Isomerism in Cycloalkanes

Chapter 4: Stereochemistry of Alkanes and Cycloalkanes- you should know;

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Conformations of Ethane, Propane, and Butane

Conformation and Stability of Cycloalkanes: The Baeyer Strain Theory
Heats of Combustion of Cycloalkanes
The Nature of Ring Strain
Cyclopropane: An Orbital View
Conformations of Cyclobutane, Cyclopentane, and Cyclohexane
Axial and Equatorial Bonds in Cyclohexane
Conformational Mobility of Cyclohexane, Monosubstituted Cyclohexanes, and Disubstituted
Cyclohexanes

Chapter 5: An Overview of Organic Reactions- You should know;

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Kinds of Organic Reactions

Using curved arrows in mechanisms
How Organic Reactions Occur(Mechanisms)
Radical and Polar (How They Occur)
An Example of a Polar Reaction: Addition of HBr to Ethylene

7. Using Curved Arrows in Polar Reaction Mechanisms

8. Describing a Reaction: Equilibria, Rates, and Energy Changes, Bond Dissociation Energies, and
Energy Diagrams , Transition States, and Intermediates
Chapter 6: Alkenes: Structure and Reactivity- You should know;
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Industrial Preparation and Use of Alkenes

Calculating a Molecules Degree of Unsaturation
Naming Alkenes
Electronic Structure of Alkenes
Cis-Trans Isomerism in Alkenes
Sequence Rules: The E,Z Designation
Alkene Stability
Electrophilic Addition of HX to Alkenes
Orientation of Electrophilic Addition: Markovnikovs Rule
Carbocation Structure and Stability
Evidence for the Mechanism of Electrophilic Addition: Carbocation Rearrangements

Chapter 7: Alkenes: Reactions and Synthesis you should know;

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Preparation of Alkenes: A Preview of Elimination Reactions

Addition of Halogens to Alkenes
Halohydrin Formation
Addition of Water to Alkenes: Oxymercuration, and Hydroboration
Addition of Carbenes to Alkenes: Cyclopropane Synthesis
Reduction of Alkenes: Hydrogenation
Oxidation of Alkenes: Hydroxylation and Cleavage

Chapter 8: Alkynes: An Introduction to Organic Synthesis- you should know;

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Electronic Structure of Alkynes

Naming Alkynes
Preparation of Alkynes: Elimination Reactions of Dihalides
Reactions of Alkynes: Addition of HX and X2
Hydration of Alkynes, Reduction of Alkynes, Oxidative Cleavage of Alkynes
Alkyne Acidity: Formation of Acetylide Anions
Alkylation of Acetylide Anions
An Introduction to Organic Synthesis (Road Map Synthesis)

Chapter 9: Stereochemistry- you should know;

1. Enantiomers and the Tetrahedral Carbon
2. Chirality , Optical Activity, and Specific Rotation
3. Sequence Rules for Specification of Configuration
4. Diastereomers and Meso Compounds
5. Molecules with More Than Two Chirality Centers
6. Racemic Mixtures and Their Resolution
7. Physical Properties of Stereoisomers
8. A Brief Review of Isomerism

9. Fischer Projections
10. Assigning R,S Configurations to Fischer Projections
11. Stereochemistry of Reactions: Addition of HBr to Alkenes, Addition of Br2 to Alkenes, and
Addition of HBr to a Chiral Alkene
Chapter 10: Alkyl Halides- you should know;
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Naming Alkyl Halides

Structure of Alkyl Halides
Preparation of Alkyl Halides
Radical Halogenation of Alkanes, and Allylic Bromination of Alkenes
Stability of the Allyl Radical- Resonance Distribution
Preparing Alkyl Halides from Alcohols
Reactions of Alkyl Halides: Grignard Reagents and Organometallic Coupling Reactions
Oxidation and Reduction in Organic Chemistry

Chapter 11: Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations-you should know
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Stereochemistry of Nucleophilic Substitution

Kinetics of Nucleophilic Substitution
The SN 2 Reaction and Characteristics of the SN 2 Reaction
The SN1 Reaction and Kinetics of the SN1 Reaction
Stereochemistry of the SN1 Reaction and Characteristics of the SN1 Reaction
Elimination Reactions of Alkyl Halides: Zaitsevs Rule
The E2 Reaction
Elimination Reactions and Cyclohexane Conformation
The Deuterium Isotope Effect
The E1 Reaction

Chapter 12: Structure Determination: Mass Spectrometry and Infrared Spectroscopy-you should
know;
1. Mass Spectrometry and Infra-Red applications
2. Interpreting Mass Spectra
3. Interpreting Mass Spectral Fragmentation Patterns
4. Mass Spectral Behavior of Some Common Functional Groups
*5. Spectroscopy and the Electromagnetic Spectrum
*6. Infrared Spectroscopy of Organic Molecules
*7. Interpreting Infrared Spectra
*8. Infrared Spectra of Hydrocarbons
*9. Infrared Spectra of Some Common Functional Groups
* Optional sections