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
SUBJECT 1. CARBOXYLIC ACIDS
Theory: Nomenclature of carboxylic acids | Physical properties of carboxylic acids | Acidity and basicity of carboxylic acids | Preparation of carboxylic acids | Oxidation of alcohols and alkenes | Organometallic compounds | Hydrolysis of nitriles | Preparation of Alkanoyl Halides | Preparation of anhydrides | Synthesis of esters from carboxylic acids | Synthesis of amides from carboxylic acids | Reaction with organometallics of carboxylic acids | Reduction to alcohols of carboxylic acids | Carboxylic acid enolates | Hell-Volhard-Zelinski | Hunsdieker reaction of carboxylic acids
Problems: Carboxylic Acid Problems
SUBJECT 2. DERIVATIVES OF CARBOXYLIC ACIDS
Order of reactivity | Acid-base behavior
- ALKANOYL HALIDES
Theory: Alkanoyl Halide Nomenclature | Reaction with water and alcohols of alkanoyl halides | Reaction with amines of alkanoyl halides | Reaction with organometallics of alkanoyl halides | Reduction to alcohols and aldehydes of alkanoyl halides
Problems: Acid Halide Problems
- ANHYDRIDES
Theory: Anhydride Nomenclature | Anhydride Reactivity
- ESTERS
Theory: Nomenclature of esters | Hydrolysis of esters | Transesterification of esters | Amides from esters | Reaction with organometallic esters | Reduction to alcohols and aldehydes of esters | Ester enolates | Claisen condensation of esters | pyrolysis of esters
Problems : Esters Problems
- AMIDES
Theory: Amide nomenclature | Amide hydrolysis | Reduction to amines and aldehydes of amides | Amide enolates and amidates | Hofmann rearrangement of amides
Problems: Amide Problems
- NITRILES
Theory: Nitrile nomenclature | Acidity and basicity | Hydrolysis of nitriles | Reaction with organometallic nitriles | Reduction of nitriles to amines and aldehydes.
Problems: Nitrile problems
SUBJECT 3. DIFUNCTIONAL COMPOUNDS
Theory: Acetylacetic synthesis | Malonic synthesis | Knoevenagel condensation | Michael's addition
SUBJECT 4. AMINES
Theory: Amine nomenclature | Physical properties and acid base of amines | Amine synthesis | Reductive Amination of Amines | Amine reactivity | Hofmann elimination of amines | Mannich reaction of amines | Removal of Cope from amines | Reaction with nitrous acid of amines | Diazomethane
Problems: Amine problems
UNIT 5. SILICON, PHOSPHORUS AND SULFUR COMPOUNDS
Theory: Phosphorus Compounds | Wittig reaction | Wadsword_Emmons | Horner-Wittig | Sulfur compounds |Thiols | Sulfides | Sulfoxide removal | Sulfur ylides | Thioacetals | Synthesis of 1,3-dithianes | silicon compounds
SUBJECT 6. STEREOCHEMISTRY II
Theory: Types of isomers | Conformational isomers | Symmetry elements | Symmetry axis | Reflection plane | Center of symmetry | Alternating axis | Elements of asymmetry | chiral center | Chirality axis | Chirality plane | Helical molecules | Notations | Prochirality | Types of ligands | Pro_R and Pro_S ligands | Faces | Racemate resolution
