Structure, Reactivity and Stereochemistry of Organic Compounds

Paper Code: 
24CHY122
Credits: 
4
Contact Hours: 
60.00
Max. Marks: 
100.00
Objective: 

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

Course Code

Course

Title

 

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.

 

 

Written examinations,

Assignments, Quiz

 

 

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.

 

12.00
Unit II: 
Structure & Reactivity

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.

 

12.00
Unit III: 
Study of Reactive Intermediates

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.

 

12.00
Unit IV: 
Stereochemistry – I

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.

 

12.00
Unit V: 
Stereochemistry – II

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.

 

Essential Readings: 
  1. Advanced Organic Chemistry: Reactions, Mechanisms and Structure, Seventh Edition; J. March; John Wiley and Sons Asia Private Limited, New Delhi, 2015.
  2. Stereochemistry: Conformation and Mechanism, Tenth Edition; P.S. Kalsi; New Age International Publishers Pvt. Ltd, New Delhi, 2019.
  3. Stereochemistry of Organic Compounds, Third Edition; D. Nasipuri; New Age International Publishers Pvt. Ltd, New Delhi, 2007.
  4. A Guidebook to Mechanism in Organic Chemistry, Sixth Edition; P. Sykes; Pearson Education, Delhi, 2011.

 

References: 
  1. Advanced Organic Chemistry Part A & B, Fifth Edition; F. A. Carey and R. J. Sundberg; Springer, US, 2007.
  2. Physical Organic Chemistry Vol. I and II, Second Edition; N. Isaacs; Longman Scientific and Technical,1995.
  3. Named Organic Reactions, Second Edition; T. Lave and A. Plagens; John Wiley and Sons, 2005.
  4. Organic Chemistry: Vol. I and II, Second Edition; Singh, Mukherjee, Kapoor; New Age International Private Limited, New Delhi, 2018.
  5. Organic Reaction Mechanism, Fourth Edition; V.K. Ahluwalia and R.K. Parashar; Narosa Publishing House, New Delhi, 2002.
  6. Stereochemistry and Mechanism through solved Problems, Third Edition; P. S. Kalsi; New Age International Pvt. Ltd., New Delhi, 2004.

 

e-Resources:

  1. https://epgp.inflibnet.ac.in/Home/ViewSubject?catid=13G8VouhmrFfuhs6rkiyTA== (P-01)
  2. https://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/sterisom.htm#start (Stereochemistry)
  3. https://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/sterism2.htm#isom9 (Stereochemistry)

 

Academic Year: 
2024-2025
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