This course will enable the students to
understand the core concepts of organic chemistry i.e. resonance, hyperconjugation, inductive effect etc. and their qualitative and quantitative treatment. The course will also provide an in-depth knowledge about the organic-chemical reactions with a focus on aromaticity, stereochemistry, reactive intermediates and their rearrangements.
Course |
Learning Outcome (at course level) |
Learning and Teaching Strategies |
Assessment Strategies |
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Course Code |
Course title |
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24DCHY712 |
Structure, Reactivity and Stereochemistry of Organic Compounds (Theory) |
CO183: Identify the different aromatic, non-aromatic, homoaromatic & antiaromatic compounds and interpret their properties. CO184: Determine and evaluate the effect of substituents on reactivity using qualitative and quantitative methods. CO185: Appraise the stability and use of reaction intermediate in skeletal and molecular rearrangements. CO186: Discuss in detail, the configurational isomerism of the molecules in the presence and absence of chiral centre(s). CO187: Elaborate all the desired aspects of conformational isomerism of molecules. CO188:Contribute effectively in course-specific interaction |
Approach in teaching: Interactive lectures, tutorials, group discussions and e-learning.
Learning activities for the students: Peer learning, e- learning, problem solving through tutorials and group discussions.
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Written examinations, assignments and quiz
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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.
A review of 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, resonance effect, field effects & steric effects. Quantitative treatment of the effect of structure on reactivity. The Hammet equation and linear free energy relationship, substituent and reaction constants & Taft equation.
Applications of HSAB principle to organic reactions.
Types, generation, structure, stability, detection and reactivity of the reactive intermediates- carbocation including 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.
Chirality and asymmetry, molecules with one, two or more chiral centres. Configuration nomenclature, D/L and R/S types of recemates 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.
Configurations, conformations 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, Prelog’s rule, 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.
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