Organic Chemistry 2

 

General Outline & Index:

Resonance and π-systems

• Conjugation and Heats of Hydrogenation

Aromatic, Anti-Aromatic, & Non-Aromatic

• Huckel’s Rule (4n+2)

• Nomenclature of Substituted Benzenes & their Intractable Common Names

Electrophilic Aromatic Substitution (S_EAr)

• Activation and De-activation
• Regiochemistry around Benzene; Directing Groups (R and I effects)
• Arenium Cation
• Synthesis of Polysubstituted Benzene Rings
  • Halogenation
  • Sulfonation
  • Friedel-Crafts Alkylation
  • Friedel-Crafts Acylation
  • Nitration
  • Diazotization
  • Smiles Rearrangement
• Sandmeyer Reaction

Nucleophilic Aromatic Substitution (S_NAr)

• Conditions Amenable for S_NAr
• Meisenheimer Intermediates
• Benzyne
  • Kine Products

Oxidation and Reduction Reactions

• Dissolving Metal Reductions
• Catalytic Hydrogenation
• Oxidation and Transition Metals

Ketones and Aldehydes

• Carbon Nucleophiles
  • Grignard Reaction
  • Cyanohydrin Synthesis
• Nitrogen Nucleophiles β
  • Imines
  • Alkylimines
  • Enamines
• Oxygen Nucleophilesβ
• Keto-Enol Tautomerization

Carboxylic Acid Derivatives and Carbonyl (Acyl) Substitution

• Acid Halides
• Acid Anhydrides
• Esters
  • Lactones
• Amides
  • Latams
• Nitriles
• Acidic and Basic Mechanisms for Acid Derivatives & Hydrolysis

Reactions at the α-Carbon

• pKa Ranges for the Carbonyl Compounds
• Enols and Enolates
• Aldol Reaction
• Aldol Condensation
• α-Halogenation/alkylation
• α,β-unsaturation carbonyl compounds (enones and enoates)
• β-oxo and β-hydroxy Carbonyl Compounds

• α,β-unsaturation carbonyl compounds (enones and enoates)
• The Michael Reaction (Conjugate addition reactions)
• HSAB (Hard/Soft Acid Base Theory)
• Claisen Condensation
• Decarboxylation
• Dieckmann Condensation
• Robinson Annulation

Pericyclic Reactions

• Molecular Orbitals and Aromatic Transitions States (Hückel’s Rule revisited)
• The Conservation of Orbital Symmetry
• Cycloaddition Reactions
  • The Diels-Alder [4+2] Reaction
  • The Retro-Diels-Alder Reaction
  • The Alder Endo Rule
  • Fused Polycyclic Compounds and their Nomenclature
• Sigmatropic Rearrangements
  • The Cope Rearrangement
  • The Claisen Rearrangement
• Stereoselectivity of Antara- and Suprafacial Migration
• Electrocyclization Reactions
  • Stereocontrol during 6π-ERC
    • Conrotation and Disrotation

Carbohydrates & Sugars

• Aldoses
• Ketoses
• The Anomeric Carbon
• Pyranoses
• Furanoses
• Alditols
• Aldaric Acids
• The Fischer Proof of the Absolute Configuration of (D)-Glyceraldehyde
• Kiliani-Fischer Reaction
• Osazones
• Tollen’s Reagent
• Haworth Projections (pronounced like Hayworth)
• Ruff Degradation

The Anomeric Effect (Negative Hyperconjugation)

• Stereoelectronic Effects between π and p-type orbitals with σ* orbitals (filled→empty)
• Glycosidic Linkages and their Terminology

Fats and Lipids

• Saponification
• Triglycerides, Saturated and Unsaturated Fatty Acids & Cholesterol
• Polyunsaturated Fatty Acids and their Common Names

Amino Acids and Proteins

• Peptide Synthesis
• The Polypeptide bond, Primary, Secondary, Tertiary, & Quaternary Structure
• Enzymes and the Active Site
• pH gradient gel Electrophoresis
• pKa and pI

Nucleotides, Nucleosides, DNA & RNA

• Purines and Pyrimidines
• Nucleotide Analogues & Pharmacology
• Transcription
• Translation

Organic Chemistry 2

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