SUBJECT 1. ALKANES
Theory: Types of Alkanes | Alkanes nomenclature | Physical properties of alkanes | Conformational isomers | Newman projection | Potential Energy Diagrams | combustion of alkanes
Problems : Alkanes problems
UNIT 2. RADICAL HALOGENATION REACTIONS
Theory: Mechanism | Polyhalogenations | Halogen reactivity | Radical stability | Product distribution | Halogenating agents
SUBJECT 3. CYCLOALKANES
Theory Nomenclature of cycloalkanes | Ring strain in cycloalkanes | Cyclopropane | Cyclobutane | Cyclopentane| Cyclohexane conformations | Substituted cyclohexanes.
Problems: Cycloalkanes problems
SUBJECT 4. STEREOCHEMISTRY
Theory: Structural isomers |
Geometric isomers | Enantiomers | Diastereomers | Enantiomer nomenclature | Racemic mixture and meso form | Optical activity | Fischer projection | R/S notation in Fischer | Molecules with several centers | Stereochemistry of the reactions | Stereospecific reaction | Separation of enantiomers.
Problems: Stereochemistry problems
SUBJECT 5. REACTIONS OF SUBSTITUTION AND ELIMINATION
S Theory N 2: Haloalkanes nomenclature |
Physical properties of haloalkanes | Mechanism of the S N 2 | Energy diagram of S N 2 | Stereochemistry of S N 2 | Ring size at S N 2 speed | Outgoing group in S N 2 | Nucleophile in SN2 | Substrate in S N 2 | Solvent in S N 2 | Theory S N 1: Mechanism of S
N 1 | SN1 energy diagram | Stereochemistry in S N 1 | Outgoing group in S N 1 | Nucleophile in S N 1 | Substrate in SN1 | Solvent in S N 1 | Competition Y N 2 and Y N 1.
Elimination Theory: Elimination Reactions E1 (Unimolecular Elimination) |
E2 (Bimolecular elimination) | Elimination with prevented bases.
Problems : Problems Y N 2 | SN1 problems | Problems Elimination
SUBJECT 6. ALKENES
Theory: Alkene nomenclature |
Structure and bond of alkenes | Dipole moment of alkenes | Double bond stability | Alkene synthesis : E2 | Saytzev and Hofmann Rules | E2 stereoselectivity | Alkene synthesis: dehydration of alcohols.
Problems: Alkene problems
SUBJECT 7. REACTIONS OF ALKENES
Theory: Catalytic hydrogenation in alkenes |
Addition of HX to alkenes | Markovnikov rule in alkenes | Addition of Water to Alkenes | Addition of halogens to alkenes | Other electrophilic additions to alkenes | Oxymercuriation-demercuriation of alkenes | Hydroboration in alkenes | MCPBA oxidation of alkenes | Opening of epoxides (oxacyclopropanes) | Oxidation with permanganate and osmium tetraoxide of alkenes | Ozonolysis of alkenes | Radical reactions of alkenes | Alkene polymerization. Problems : Alkene reaction problems
SUBJECT 8. ALKYNES
Theory : Alkyne nomenclature | Structure and bond in alkynes | Physical properties of alkynes | Acidic hydrogen in alkynes | Triple bond stability in alkynes | Alkyne isomerization | Allenes | Alkynes by double elimination | Alkynes by alkylation | Alkyne hydrogenation | Monoelectronic reduction of alkynes | Hydroboration of alkynes | Addition of HX, halogens and water to alkynes | Cationic cyclizations in alkynes.
Problems: Alkyne problems
SUBJECT 9. ALLYLIC SYSTEMS
Theory: Allyl system: Resonance | SN1 Reactions in Allylic Systems | Kinetic and thermodynamic control in allylic systems | SN2 reactions in allylic systems | SN2´ reaction in allylic systems | Halogenation by free radicals | Give us conjugates.
UNIT 10. DIELS-ALDER REACTION
Theory: Diels-Alder Mechanism | Diels-Alder stereochemistry | Diels-Alder with Alkynes | photochemical cycloadditions | Electrocyclic reactions.
SUBJECT 11. ALCOHOLS
Theory: Nomenclature and p. physics of alcohols | Acidity and basicity of alcohols | Alcohol synthesis | Reduction with hydrides to obtain alcohols | Organometallic | Organometallics in alcohol synthesis | Preparation of alkoxides from alcohols | rearrangement of carbocations | Transposition mechanism | degenerate transposition | Rearrangement to hydroxycarbocation | Rearrangement of 2,2-dimethyl-2-propanol | Haloalkanes from alcohols | alcohol oxidation.
Problems: Alcohol problems
SUBJECT 12. ETHERS
Theory: Ethers nomenclature and properties |
Williamson synthesis of ethers | Ethers from alcohols | Protecting groups | Ethers via SN1 | Opening of oxacyclopropanes (epoxides). Problems: Ethers Problems
SUBJECT 13. ALDEHYDES AND KETONES
Theory: Aldehyde and ketone nomenclature | Physical properties of aldehydes and ketones | Preparation of aldehydes and ketones | Addition of water and alcohols to aldehydes and ketones | Hydrate formation | Hemiacetals and acetals | Cyclic acetals | Thioacetals | Addition of ammonia and derivatives to aldehydes and ketones | Imine formation | Oxime formation | Hydrazone formation | Azine formation | Formation of semicarbazones | Phenylhydrazine assay | Wolff-Kishner reduction of aldehydes and ketones | Clemmensen reduction of aldehydes and ketones | Enamine formation | Cyanohydrin formation | Wittig reaction of aldehydes and ketones | Sulfur ylides | Baeyer-Villiger with aldehydes and ketones | Fehling and Tollens test for aldehydes and ketones.
Problems: Carbonyl problems
SUBJECT 14. ENOLS AND ENOLATES
Theory: Enols and enolates | Alkylation of aldehyde and ketone enolates | HD exchange in aldehydes and ketones | Halogenation and isomerization of aldehydes and ketones | Aldol condensation | Preparation of alpha-beta unsaturated | Additions to alpha-beta unsaturated | Michael and Robinson's reactions.
Problems: Enol and enolate problems
SUBJECT 15. BENZENE
Theory: Benzene Nomenclature | Huckel's rule in aromatic systems (benzene) | Halogenation of benzene | Nitration of benzene | Sulfonation of benzene | Alkylation of benzene | Acylation of benzene | Activating and deactivating groups in benzene | Ipso substitution of benzene | Benzine | Benzyl position in benzene | Oxidation of benzene side chains
Issues: Benzene Issues