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Structural Determination

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SUBJECT 3. INFRARED SPECTROSCOPY

SUBJECT 4. NUCLEAR MAGNETIC RESONANCE (NMR)

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SUBJECT 1. 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

SUBJECT 2. NATURAL PRODUCTS sugar


UNIT 3. REACTION MECHANISMS
  • Tools to determine a mechanism : Identify products. Identify intermediates. Isotopic labeling. Product stereochemistry. Solvent effect.
  • Kinetic data: Definition of speed. Kinetic equations. Consecutive reactions. Nitration of benzene Arrhenius theory. Transition state theory. competitive reactions. Curtin-Hammet principle. Hammond principle.
  • Isotope effect: Primary isotope effect. Secondary isotope effect.
  • Hammett's equation.

SUBJECT 4. REACTIONS OF SUBSTITUTION AND ELIMINATION

  • Concepts in Y N 2: Kinetics. Stereochemistry. Solvent. Nucleophile and nucleophobic. Substrate structure.
  • Concepts in S N 1: Kinetics. Stereochemistry. Solvent. Substratum. anchimeric assistance. Nonclassical carbocations.
  • Elimination reactions: Elimination 1,2. Elimination 1.4. Elimination 1.1. Elimination 1.3. Fragmentation. E1 (Unimolecular elimination). E2 (bimolecular elimination). E1cb. Stereochemistry of elimination reactions. Regiochemistry of elimination reactions. pyrolytic removals. Elimination of Hofmann and Cope


SUBJECT 5. ORGANIC SYNTHESIS

  • Formation of single bonds: Alkylation of enolates. Alkylation of enamines. Imines and lithiated enamines. Stereoselective alkylation. aldol condensation. Michael and Robinson. Claisen condensation. Acetylacetic and malonic synthesis. Formation of dianions. Umpolung reactions.
  • Formation of double bonds: E2. Pyrolysis of esters. Elimination of Cope. Hofmann elimination. Sulfoxide removal. Sulfoxide-sulfenate rearrangements. Wittig reactions. Wittig. Wadsword-Emmons. Horner-Wittig. Peterson. Sulfur ylides. Shapiro.
  • Diels-Alder: Stereochemistry. Regiochemistry.
  • Carbenes: Singlet and triplet carbenes. Synthesis of carbenes : Elimination 1.1. Decomposition of diazo compounds. Decomposition of tosylhydrazones. Reactivity of carbenes: Cyclopropanation. Simmons-Smith reaction. CH insert. Arndt-Eistern. Hofmann and wolf transposition.
SUBJECT 6. OXIDATION REDUCTION REACTIONS (REDOX)
  • Oxidation of benzylic H. Oxidation of H. allylics
  • Oxidation of alcohols: Derivatives of ac. chromic. manganese dioxide. Alkoxysulfonium salts. Swern oxidation. Oppenaver oxidation
  • Olefin oxidation: Oxidation with permanganate and osmium tetroxide. Prevost reaction. Woodward's reaction. Alkene epoxidation. Epoxy opening. ozonolysis. Oxidation with periodic acid.
  • Oxidation of ketones: Oxidation to alpha-beta unsaturated: Baeyer-Villiger. Oxidation to alpha-hydroxyketones.
  • Reduction reactions: Hydrogenation. Acyloinic condensation. Non-metallic hydrides. Clemmensen. Wolff-kisnner. thioacetals Alkynes with Na/NH 3 . Birch reduction. Obtaining 1,2-symmetrical diols

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SUBJECT 1. ALKANESbutane

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 cyclopentane

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 iodopropane

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 No 1: Mechanism of the 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 2 pentene

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 2 butine

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 propanediol

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 carbonyl

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 ab unsaturated

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 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 16. CARBOXYLIC ACIDS

benzoic acid

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 17. 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 methyl butanoate

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 18. DIFUNCTIONAL COMPOUNDS

Theory: Acetylacetic synthesis | Malonic synthesis | Knoevenagel condensation | Michael's addition

 

SUBJECT 19. AMINES methylpropanamine

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 20. 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

 

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condensed heterocycle SUBJECT 1. NOMENCLATURE OF HETEROCYCLES

Theory: Common names | Hantzch–Widman nomenclature | Partially unsaturated heterocycles | The indicated hydrogen | Heterocycle numbering | Heterocycles as substituents | Replacement nomenclature.

UNIT 2. AROMATICITY IN HETEROCYCLES

Theory: What is an aromatic heterocycle? ! Aromatic heterocycles and their types! Criteria to determine aromaticity in heterocycles. | Tautomerism in aromatic heterocycles | Non-aromatic heterocycles, influence of ring stresses on their properties | anomeric effect.

condensed heterocycle 02 UNIT 3. SYNTHESIS OF HETEROCYCLES (I): CYCLING REACTIONS

Theory: Synthesis of heterocycles by cyclization reactions | Reagents in cyclization reactions | Classification of nucleophilic attacks (Baldwin's Rules) | Cycle formation by S N 2 | Nucleophilic addition and addition elimination processes on sp 2 carbons. | Cyclization on sp carbon atoms | Cyclization of carbenes, nitrenes and radicals.

SUBJECT 4. SYNTHESIS OF HETEROCYCLES (II): CYCLOADDITION REACTIONS

Theory: hetero-Diels-Alder cycloadditions: frontier orbitals. | Hetero-Diels-Alder cycloadditions in synthesis of heterocycles. | Hetero-cycloadditions [2+2]. | Chelotropic reactions | 1,3-dipolar cycloadditions | Energies and coefficients of the frontier orbitals of 1,3-dipoles | Regio- and stereoselectivity of the 1,3-dipolars. | Most important dipoles, preparation and reactivity.

UNIT 5. 6-MEMBED HETEROCYCLES: PYRIDINE

Theory: Hantzsch synthesis | Chichibabin synthesis | Basicity | Alkylation and Acylation | Formation of N-oxides | Electrophilic substitution | Electrophilic substitution in position 4 | Lithiation reaction | Nucleophilic addition reactions | Substitution reactions | Pyridine | Alkyl- and vinylpyridines

quinoline SUBJECT 6. NOMENCLATURE OF CONDENSED HETEROCYCLES

Theory: Choice of base component | Peripheral numbering of the global heterocycle | Examples of nomenclature of fused heterocycles.

SUBJECT 7. QUINOLINE AND ISOQUINOLINE

Theory: Skraup Synthesis | Combes Synthesis | Friedlander synthesis | Bischer-Napieralski synthesis | Pictet Spengler Synthesis | Pomeranz Fritsch Synthesis | Reactivated with the lone pair of nitrogen | Electrophilic substitution reactions | Lithiation reaction | Nucleophilic addition reactions | Nucleophilic substitution reactions | Derivatives of alkyl- and vinylquinolines and isoquinolines.

UNIT 8. 6-MEMBED HETEROCYCLES WITH 2 OR MORE HETERO ATOMS: DIAZINES

Theory: Di-, tri-, tetrazines general concepts | Reactions with the lone pair of nitrogen (basicity and nucleophilicity) | Electrophilic substitution | Nucleophilic substitution |

SUBJECT 9. HETEROCYCLES OF 5 MEMBERS: PYRROL, TIOPHENE AND FURAN

Theory: Acid behavior | Electrophilic substitution: Nitration, halogenation, sulfonation, Vilsmeier, Mannich, acetylation | Cycloaddition reactions in furan | Derivatives | Furan opening | Paal–Knorr synthesis | Synthesis by 1,3-dipolar | Hantzsch synthesis of pyrrole.

indole SUBJECT 10. HETEROCYCLES OF 5 CONDENSED MEMBERS: INDOL

Theory: Acid behavior | Electrophilic substitution reactions | Electrophilic substitution with position 3 occupied | Ring expansion | Fisher synthesis | Madelung synthesis

UNIT 11. 5-MEMBED HETEROCYCLES WITH 2 OR MORE HETERO ATOMS: AZOLES

Theory:

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organic chemistry Article Count:  17