STRUCTURE, REACTIVITY AND STEREOCHEMISTRY OF ORGANIC COMPOUNDS

Aromaticity in benzenoid and non-benzenoid compounds, alternant and non-alternant hydrocarbons, Huckel’s rule and Möbius system, energy level of π molecular orbitals in three to eight membered monocyclic systems having conjugation, annulenes, fullerenes, antiaromaticity, homoaromaticity, PMO approach, steric inhibition to resonance.
Bonds weaker than covalent- addition compounds, phase transfer catalysis and crown ethers, cryptands, inclusion compounds, cyclodextrins, catenanes, rotaxanes and Kekulene. H-bonding and its effect on organic compounds.

Types of mechanisms and reactions, methods of determining reaction mechanism, thermodynamic and kinetic control of reactions, Hammond’s postulate, Curtin- Hammett principle, isotope effects.
Effect of structure on reactivity
Qualitative treatment- resonance effect, field effects & steric effects.
Quantitative treatment -the Hammet equation, linear free energy relationship, substituent and reaction constants, Taft equation.

Types, generation, structure, stability, detection and reactivity of the reactive intermediates- carbocation , non-classical carbocation, carbanion, free radical, radical anion, carbene, nitrene, benzyne, nitrenium ion. Electrophiles and nucleophiles.
Molecular rearrangements involving above intermediates viz. Wagner - Meerwein, Pinacol-Semipinacol, Benzil-Benzilic acid, Hoffmann,  Curtius,  Lossen,  Schmidt,  Beckmann,  Naber, Favorskii, Wittig, Riemer– Tiemann reaction. Dissolving metal reduction.

Configuration, chirality and asymmetry, molecules with one, two or more chiral centres, configuration nomenclature, Prelog’s rule, D/L and R/S types of racemates and methods of resolution.
Prochirality - Topicity of ligands and faces and their nomenclature, stereogenicity, pseudoasymmetry, planar chirality, axial chirality, optical purity, chirogenicity, stereogenic and prochiral centres.
Optical activity in the absence of chiral carbons - biphenyls, allenes, alkyldienes, cycloalkyldienes, spiranes, ansacompounds, adamantanes, and cyclophanes, chirality due to helical shape (P & M), chirality in the compounds containing N, S and P.

Conformation and stability of cyclohexanes (mono-, di-, and trisubstituted), cyclohexenes, cyclohexanones, halocyclohexanones, decalins, decalols and decalones, effect of conformation on reactivity, strain in cycloalkanes.
Chiral synthesis, stereoselective and stereospecific synthesis, Felkin-anh rule, CD, ORD, octant rule, Cotton effect and their application in determination of absolute and relative configuration and conformation, the axial haloketone rule.
Chiral auxiliary and chiral pool.