Organic Chemistry II

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Synthesizing Alcohols

• Acid Catalyzed Hydration of Alkenes
• Oxymercuration
• Hydroboration/Oxidation
• Osmylation-OsO4(Osmium Tetroxide)

Alcohol Reactions

• Converting Alcohols into Halides
• SOCl2 with Non-nucleophilic Base
• PBr3
• Mesylates and Tosylates with Non-Nucleophilic Base
• Acid Catalyzed Dehydration of Alcohols
• Pinacol Rearrangements
• Oxidation of Alcohols with PCC and Jones(H2CrO4) Reagents
• Williamson Ether Synthesis
• Acid Catalyzed Cleavage of Ethers
• Protecting Alcohol Groups with TMS (Trimethylsilyl)

Organometallics

• Grignard Reagent
• Gilman Reagent
• Simmon-Smith Cyclopropanation

Ketone and Aldehyde (Carbonyl) Reactions

• Phosphonium Ylide Reactions
• Hemiacetals/Acetals/Cyclic Acetals (Oxygen Nucleophiles)
• Imines/Enamines (Nitrogen Nucleophiles)
• Wolf-Kishner Reduction

Reducing Agents

• H2, Nickel (Ni) or Platinum (Pt)
• Sodium Borohydride (NaBH4)
• Rhodium
• NaBH3CN
• LiAlH4

Carboxyllic Acid Derivatives

• Acid (Acyl) Chloride
• Acid Anhydrides
• Esters
• Amides
• Nitriles

Enolate Reactions

• Keto-Enol Tautomerization
• Aldol
• Crossed Aldol
• Intramolecular Aldol
• Retrosynthesis (Aldol)
• Claissen
• Crossed Claissen
• Intramolecular Claissen
• Retrosynthesis (Claissen)
• Michael
• Retrosynthesis (Michael)
• Robinson Annulation
• Retrosynthesis (Robinson Annulation)

Aromaticity

• Introduction to Aromaticity
• Aromatic vs. Antiaromatic vs. Nonaromatic
• Aromatic Cations and Anions

Electrophilic Aromatic Substitution Reactions with Benzene

• Halogenation
• Oxidation
• Friedel Crafts Alkylation
• Friedel Crafts Acylation
• Nitration
• Directing Groups
• Introduction to Electrophilic Aromatic Substitution
• Mechanism for Electrophilic Aromatic Substitution
• Sulfonation