Organic Chemistry Reaction Mechanisms - Coursebook

I. Solvents
	I. 1. Definition
	I. 2. Solvent Classification
		I. 2. 1. Apolar Solvents
		I. 2. 2. Polar Solvents
			I. 2. 2. 1. Protic Solvents
			I. 2. 2. 2. Aprotic Solvents
	I. 3. Solubility
II. Reactants
	II. 1. Substrate
		II. 1. 1. Carbocation
			II. 1. 1. 1. Definition and Structure
			II. 1. 1. 2. Stability
				Resonance
				Hyperconjugation
				Inductive Effect
		II. 1. 2. Carbanion
			II. 1. 2. 1. Definition and Structure
			II. 1. 2. 2. Stability
				Resonance
				Hybridization
				Inductive Effect
		II. 1. 3. Free-radical Carbon
			II. 1. 3. 1. Definition and Structure
			II. 1. 3. 2. Stability
				Resonance
				Hyperconjugation
				Inductive Effect
		II. 1. 4. Carbene
			II. 1. 4. 1. Definition and Structure
			II. 1. 4. 2. Singlet Carbenes
			II. 1. 4. 3. Triplet Carbene
			II. 1. 4. 4. Stability
	II. 2. Leaving Groups
		II. 2. 1. Nucleofuges
		II. 2. 2. Electrofuges
	II. 3. Nucleophiles
		II. 3. 1. Types of Nucleophiles
			II. 3. 1. 1. Neutral Nucleophiles
			II. 3. 1. 2. Charged Nucleophiles
		II. 3. 2. Nucleophilicity
	II. 4. Electrophiles
III. Reaction Mechanisms
	III. 1. Substitution Reactions
		III. 1. 1. Free-radical Substitution Reactions
			III. 1. 1. 1. Alkanes Halogenation
				Control of Free Radical Halogenation
				Relative Reactivity and Selectivity of Halogens
			III. 1. 1. 2. Allylic and Benzylic Halogenation
		III. 1. 2. Nucleophilic Substitution Reactions
			III. 1. 2. 1. Nucleophilic Aliphatic Substitution Reactions
				Unimolecular Nucleophilic Substitution Reactions SN1
					Reaction Conditions
				Bimolecular Nucleophilic Substitution Reactions SN2
					Reaction Conditions
				Internal Nucleophilic Substitution SNi
			III. 1. 2. 2. Nucleophilic Aromatic Substitution Reactions
				SNAr Reaction
				SN1 Aromatic Reaction
				SRN1 Reaction
			III. 1. 2. 3. Nucleophilic Substitution of Carboxylic acids and their Derivatives
				Reactivity of Carboxylic Acids and their Derivatives
		III. 1. 3.  Electrophilic Substitution Reactions
			III. 1. 3. 1. Electrophilic Aromatic Substitution Reactions SEAr
				Common Reactions
				Regioselectivity
					Mono-substituted Benzenes
					Disubstituted Benzenes
					Polycyclic Arenes “Naphthalene”
					Heteroaromatic Compounds
				Reactivity
	III. 2. Elimination Reactions
		III. 2. 1. α ( Elimination Reactions
			III. 2. 1. 1. Formation of Carbenes
		III. 2. 2. β ( Elimination Reactions
			Reaction Conditions
			III. 2. 2. 1. Regiochemistry and Stereochemistry
				Reaction Conditions
			III. 2. 2. 2. Regiochemistry and Stereochemistry
		III. 2. 3. γ( Elimination Reactions
			III. 2. 3. 1. Freund Reaction
	III. 3. Competition between SN1, SN2, E1, and E2
	III. 4. Addition Reactions
		III. 4. 1. Nucleophilic Addition Reactions
			III. 4. 1. 1. Nucleophilic Addition Reactions to Aldehydes and Ketones
				Reactivity of Aldehydes and Ketones
				Common Reactions of Aldehydes and Ketones
		III. 4. 2. Electrophilic Addition Reactions
			III. 4. 2. 1. General mechanisms
			III. 4. 2. 2. Regeochemistry and Stereochemistry
			III. 4. 2. 3. Dihalogenation Reaction
				Regiochemistry and Stereochemistry
			III. 4. 2. 4. Halogenation Reaction
				Regiochemistry and Stereochemistry
			III. 4. 2. 5. Hypohalogenation Reaction
				Regiochemistry and Stereochemistry
			III. 4. 2. 6. Hydrohalogenation Reaction
				Alkenes
					Regiochemistry and Stereochemistry
				Conjugated Dienes
					Regiochemistry and Stereochemistry
				Alkynes
			III. 4. 2. 7. Acid Catalyzed Hydration
				Alkenes
					Regiochemistry and Stereochemistry
				Alkynes
			III. 4. 2. 8. Oxymercuration-Demercuration Hydration
				Alkenes
					Regiochemistry and Stereochemistry
			III. 4. 2. 9. Hydroboration Oxidation
				Alkenes
					Regiochemistry and Stereochemistry
				Alkynes
		III. 4. 3. Concerted Addition Reactions
			III. 4. 3. 1. Addition of Carbenes
				Singlet Carbenes
				Triplet Carbenes
				Simmons-Smith Reaction
			III. 4. 3. 2. Epoxidation
				Regiochemistry and Stereochemistry
			III. 4. 3. 3. Hydrogenations Reaction
				Alkenes Hydrogenation
					Regiochemistry and Stereochemistry
				Alkynes Hydrohalogenation
		III. 4. 4. Free-radical Addition Reaction
			Regiochemistry and Stereochemistry
	III. 5. Oxidation Reactions
		III. 5. 1. Alkenes
			III. 5. 1. 1. Ozonolysis
			III. 5. 1. 2. Oxidation with Osmium tetroxide
				Regiochemistry and Stereochemistry
			III. 5. 1. 3. Oxidation with Potassium Permanganate
				Regiochemistry and Stereochemistry
			III. 5. 1. 4. Acid Catalyzed Oxidation of Peroxides
				Regiochemistry and Stereochemistry
		III. 5. 2. Alcohols
			III. 5. 2. 1. Jones Oxidation
			III. 5. 2. 2. With K2Cr2O7 (Na2Cr2O7) ; H2SO4
			III. 5. 2. 3. Oxidation with Chromium-Based Reagents
			III. 5. 2. 4. Oxidation with Sodium Hypochlorite NaOCl
			III. 5. 2. 5. Swern Oxidation
	III. 6. Reduction Reactions
		III. 6. 1. Reduction of Alkenes and Alkynes
		III. 6. 2. Reduction of Benzene
			III. 6. 2. 1. Catalytic Hydrogenation
			III. 6. 2. 2. Birch Reduction
				Regiochemistry
		III. 6. 3. Reduction of Carbonyl Compounds
			III. 6. 3. 1. With NaBH4 and LiBH4
			III. 6. 3. 2. With LiAlH4
			III. 6. 3. 3. With DIBAL
			III. 6. 3. 4. Clemmensen Reduction (Aldehydes and Ketones)
			III. 6. 3. 5. Wolff–Kishner Reduction (Aldehydes and Ketones)
			III. 6. 3. 6. Rosenmund Reduction
			III. 6. 3. 7. Mozingo Reduction
			III. 6. 3. 8. Luche Reduction
IV. Selection of Named Reactions
	IV. 1. Grignard Reaction
	IV. 2. Aldol Reaction
	IV. 3. Michael Reaction
	IV. 4. Knoevenagel Reaction
	IV. 5.  Claisen Reaction
	IV. 6. Robinson Annulation
	IV. 7. Diels-Alder Reaction
	IV. 8. Beckmann Rearrangement
	IV. 9. Wurtz Reaction
	IV. 10. Witting Reaction