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Structure, Reactivity and Stereochemistry of Organic Compounds | Chemistry

Structure, Reactivity and Stereochemistry of Organic Compounds

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Paper Code: 
CHY 122
Contact Hours: 
60.00
Objective: 

To learn the basics of organic chemistry, three dimensional concepts of molecules, elements of symmetry and stereochemistry.

12.00
Unit I: 
Aromaticity

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.

 

12.00
Unit II: 
Structure and Reactivity

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 free energy relationship, substituent and reaction constants & Taft equation.

Applications of HSAB principle to organic reactions.

12.00
Unit III: 
Study of Reactive Intermediates

Types, generation, structure, stability, detection and reactivity of the reactive intermediates- carbocation including non-classical carbocation, carbanion, free radical,  radical anion, carbene,  nitren, 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.

12.00
Unit IV: 
Stereochemistry – I

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, alkyledines, cycloalkyledines, spiranes, ansa compounds , adamantanes, and cyclophanes, chirality due to helical shape (P & M), chirality in the compounds containing N, S and P.

12.00
Unit V: 
Stereochemistry - II

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, Steroselective 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 auxillary and chiral pool.

Essential Readings: 
  1. Advanced Organic Chemistry: Reactions, Mechanisms and Structure; Fourth Edition; J. March; John Wiley and Sons Asia Private Limited, New Delhi, 2007.
  2. Advanced Organic Chemistry Part A & B; Fourth Edition; F. A. Carey and R. J. Sundberg; Kluwer Academic/Plenum Publishers, New York, 2001.
  3. Stereochemistry: Conformation and Mechanism; Fifth Edition; P.S. Kalsi; New Age International Publishers Pvt. Ltd, New Delhi, 2004.
  4. Physical Organic Chemistry Vol. I and II; Second Edition; N. Isaac; Longman.
  5. Named Organic Reactions; Second Edition: T. Lave and A. Plagens; John Wiley and Sons, 2005.
  6. Organic Chemistry: Vol. I and II; Singh, Mukherjee, Kapoor; Wiley Eastern Limited, New Delhi, 2003.
  7. Organic Reaction Mechanism; Fourth Edition; V.K.Ahluwalia and R. K. Parashar; Narosa Publishing House, 2002.
  8. Stereochemistry of Organic Compounds; Third Edition; D. Nasipuri; New Age International Publishers Pvt. Ltd, New Delhi, 2007.
  9. Stereochemistry and Mechanism through solved Problems; Third Edition; P. S. Kalsi; New Age International Pvt. Ltd., New Delhi, 2004. 
Academic Year: