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Organic Chemistry II (CHE251) Final Exam Review Topics: Comprehensive Study Notes

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Intro to Organic Chemistry

Atomic Structure

Wave Function

Molecular Orbitals

Sigma and Pi Bonds

Octet Rule

Bonding Preferences

Formal Charges

Skeletal Structure

Lewis Structure

Condensed Structural Formula

Degrees of Unsaturation

Constitutional Isomers

Resonance Structures

Hybridization

Molecular Geometry

Electronegativity

Intermolecular Forces

How To Determine Solubility

Functional Groups

Reaction Mechanism

Acids and Bases

Equilibrium Constant

pKa

Acid Base Equilibrium

Ranking Acidity

IUPAC Naming

Alkyl Groups

Naming Cycloalkanes

Naming Alkyl Halides

Naming Alkenes

Cis vs Trans

Conformational Isomers

Newman Projections

Drawing Newman Projections

Barrier To Rotation

Ring Strain

Axial vs Equatorial

Cis vs Trans Conformations

Equatorial Preference

Chair Flip

Calculating Energy Difference Between Chair Conformations

A-Values

Decalin

Oxidizing and Reducing Agents

Constitutional Isomers vs. Stereoisomers

Chirality

Test 1:Plane of Symmetry

Test 2:Stereocenter Test

R and S Configuration

Enantiomers vs. Diastereomers

Meso Compound

Test 3:Disubstituted Cycloalkanes

What is the Relationship Between Isomers?

Fischer Projection

R and S of Fischer Projections

Optical Activity

Enantiomeric Excess

Calculations with Enantiomeric Percentages

Organic Chemistry Reactions

Energy Diagram

Gibbs Free Energy

Enthalpy

Entropy

Nucleophilic Substitution

Good Leaving Groups

SN2 Reaction

SN1 Reaction

Carbocation Stability

Carbocation Intermediate Rearrangements

Hammond Postulate

Substitution Comparison

E2 Mechanism

Beta Hydrogen

E2 - Anti-Coplanar Requirement

E1 Reaction

Solvents

Leaving Groups

Nucleophiles and Basicity

SN1 SN2 E1 E2 Chart (Big Daddy Flowchart)

Cumulative Substitution/Elimination

Alkene Stability

Zaitsev Rule

Dehydrohalogenation

Alcohol Nomenclature

Dehydration Reaction

Alcohol Synthesis

Addition Reaction

Markovnikov

Hydrohalogenation

Acid-Catalyzed Hydration

Oxymercuration

Hydroboration

Halogenation

Halohydrin

Alkyne Hydrohalogenation

Alkyne Halogenation

Alkyne Hydration

Alkyne Hydroboration

Acetylide

Alkynide Synthesis

Alkane Halogenation

Retrosynthesis

Oxidizing and Reducing Agents

Hydrogenation

Ozonolysis

Oxidative Cleavage

Epoxidation

Dihydroxylation

Birch Reduction

Purpose of Analytical Techniques

Mass Spectrometry

Infrared Spectroscopy

NMR Spectroscopy

Radical Reaction

Radical Stability

Free Radical Halogenation

Radical Selectivity

Allylic Bromination

Anti Markovnikov Addition of Br

Free Radical Polymerization

Radical Synthesis

Conjugation Chemistry

Stability of Conjugated Intermediates

Allylic Halogenation

Reactions at the Allylic Position

Conjugated Hydrohalogenation (1,2 vs 1,4 addition)

Diels-Alder Reaction

Aromaticity

Huckel's Rule

Pi Electrons

Aromatic Hydrocarbons

Electrophilic Aromatic Substitution

Benzene Reactions

EAS:Halogenation Mechanism

EAS:Nitration Mechanism

EAS:Friedel-Crafts Alkylation Mechanism

EAS:Friedel-Crafts Acylation Mechanism

Electron Withdrawing Groups

EAS:Ortho vs. Para Positions

Side-Chain Halogenation

Side-Chain Oxidation

Reactions at Benzylic Positions

Nucleophilic Aromatic Substitution

Oxidation of Phenols to Quinones

Reactions of Pyrrole, Furan, and Thiophene

Directing Effects in Substituted Pyrroles, Furans, and Thiophenes

EAS Reactions of Pyridine

SNAr Reactions of Pyridine

Side-Chain Reactions of Substituted Pyridines

Nucleophilic Addition

Alcohol Protecting Groups

Preparation of Organometallics

Grignard Reaction

Organometallics on Ketones

Protecting Alcohols from Organometallics

Carboxylation

Naming Aldehydes

Naming Ketones

Cyanohydrin

Wittig Reaction

Hydrates

Hemiacetal

Acetal

Acetal Protecting Group

Thioacetal

Imine vs Enamine

Addition of Amine Derivatives

Ketone and Aldehyde Synthesis Reactions

    Naming Carboxylic Acids

    Diacid Nomenclature

    Naming Nitriles

    Nitrile to Ketone

    Review of Nitriles

    Acid Chloride Nomenclature

    Naming Anhydrides

    Naming Esters

    Naming Amides

    Carboxylic Acid Derivatives

    Nucleophilic Acyl Substitution

    Carboxylic Acid to Acid Chloride

    Lactones, Lactams and Cyclization Reactions

    Fischer Esterification

    Acid-Catalyzed Ester Hydrolysis

    Saponification

    Transesterification

    Tautomerization

    Enolate

    Acid-Catalyzed Alpha-Halogentation

    Base-Catalyzed Alpha-Halogentation

    Haloform Reaction

    Hell-Volhard-Zelinski Reaction

      Decarboxylation Mechanism

      Enolate Alkylation and Acylation

      Beta-Dicarbonyl Synthesis Pathway

      Acetoacetic Ester Synthesis

      Malonic Ester Synthesis

      Condensation Reactions

      Aldol Condensation

      Directed Condensations

      Crossed Aldol Condensation

      Claisen-Schmidt Condensation

      Claisen Condensation

      Intramolecular Aldol Condensation

      Conjugate Addition

      Michael Addition

      Robinson Annulation