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 Outcomes (COs):
Course |
Learning outcome (at course level) |
Learning and Teaching Strategies |
Assessment Strategies |
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Course Code |
Course Title |
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24CHY122 |
Structure, Reactivity and Stereochemistry of Organic Compounds (Theory) |
CO7: Identify the different aromatic, non-aromatic, homoaromatic & antiaromatic compounds and interpret their properties. CO8: Determine and evaluate the effect of substituents on reactivity using qualitative and quantitative methods. CO9: Appraise the stability and use of reaction intermediates in skeletal and molecular rearrangement. CO10: Discuss in detail, the configurational isomerism of the molecules in the presence and absence of chiral centre(s). CO11: Elaborate all the desired aspects of conformational isomerism of molecules. CO12: 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, 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.
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- 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.
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