Course Objectives :
The course aims to make the students 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 outcomes (at course level) |
Learning and teaching strategies |
Assessment Strategies |
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Paper Code |
Paper Title |
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CHY 122 |
Structure, Reactivity and Stereochemistry of Organic Compounds |
The students will be able to-
CO7- identify the different aromatic, non-aromatic, homoaromatic & antiaromatic compounds and interpret their properties. CO8- evaluate the stability of various acyclic and cyclic systems using various stereoelectronic effects and correlate their reactivities. CO9- describe various types of reactive intermediates and factors affecting their stability . CO10- practice the skeletal and molecular rearrangements involving various reactive intermediates CO11- identify and differentiate prochirality and chirality at centers, axis, planes and helices and determine the absolute configuration. CO12- apply various rules for determining stereoselectivity of various organic transformations
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Interactive lectures
Discussions
Tutorials
Quiz
Problem solving
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Written test
Google quiz
Assignment
Tutorial
Group activity
Semester end examination
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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.
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.
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.