Structure, Reactivity and Stereochemistry of Organic Compounds

Paper Code: 
24DCHY712
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: 

Course

Learning Outcome

(at course level)

Learning and Teaching Strategies

Assessment Strategies

Course Code

Course

title

 

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.

 

 

Written examinations,

assignments and  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 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 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,  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

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.

 

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, 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.

 

Essential Readings: 
  1. Organic Chemistry, Sixth Edition; R. T. Morrison, R. N. Boyd; Pearson Education India, New Delhi, 2017.
  2. Advanced Organic Chemistry: Reactions, Mechanisms and Structure, Seventh Edition; J.   March; John Wiley and Sons Asia Private Limited, New Delhi, 2015.
  3. Stereochemistry Conformation and Mechanism, P.S. Kalsi; New Age International, 2005.
  4. Organic Chemistry: Vol. I and II, Singh, Mukherjee, Kapoor; Second Edition; New Age International Private Limited, New Delhi, 2018.

 

References: 
  1. Stereochemistry of Organic Compounds , E. L Eliel,. & S. H. Wilen; Wiley, London, 1994.
  2. Organic Chemistry, Vol. I, Sixth Edition; I.L. Finar; Pearson Education, New Delhi 2002.
  3. Organic Chemistry, Sixth Edition; G. Marc Loudon, J. Parise; WH Freeman, New York, 2015.
  4. Stereochemistry of Organic Compounds, Third Edition; D. Nasipuri; New Age International Publishers Pvt. Ltd, New Delhi, 2007.
  5. Stereochemistry and Mechanism through solved Problems, Third Edition; P. S. Kalsi; New Age International Pvt. Ltd., New Delhi, 2004.

 

e-Resources:

  1. https://www.youtube.com/watch?v=yzfcrwJ37kI (Unit IV & V)
  2. https://epgp.inflibnet.ac.in/epgpdata/uploads/epgp_content/S000005CH/P000656/M026149/ET/1515563870CHE_P1_M8_etext.pdf (Unit I)
  3. https://epgp.inflibnet.ac.in/Home/ViewSubject?catid=13G8VouhmrFfuhs6rkiyTA== (P-01)
  4. https://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/sterisom.htm#start (Unit IV & V)
  5. https://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/sterism2.htm#isom9 (Unit IV & V)

 

Academic Year: