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Home > STRUCTURE, REACTIVITY AND STEREOCHEMISTRY OF ORGANIC COMPOUNDS

STRUCTURE, REACTIVITY AND STEREOCHEMISTRY OF ORGANIC COMPOUNDS [1]

Paper Code: 
D-CHY 712
Credits: 
4
Contact Hours: 
60.00
Max. Marks: 
100.00
Objective: 

Course Objective(s):

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 and gain an in-depth knowledge about the organic-chemical reactions with a focus on aromaticity, stereochemistry, reactive intermediates and their rearrangements.

 

Course Outcomes (COs):

Course Outcomes

Teaching Learning

Strategies

Assessment

Strategies

On completion of this course, the students will be able to-

CO136: identify the different electronic effects and apply the knowledge of to solve the mechanistic problems.

CO137:apply the concepts of configurational and conformational isomerism in different organic compounds.

CO138: identify and differentiate prochirality and chirality at centers, axis, planes and helices and determine the absolute configuration.

CO139:practice the skeletal and molecular rearrangements involving various reactive intermediates.

CO140: identify the different aromatic, nonaromatic, homoaromatic and antiaromatic compounds and interpret their properties.

  • Interactive lectures
  • Group discussions
  • Digital learning

 

  • Oral and 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.

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

 

References: 

SUGGESTED READINGS:

  • Stereochemistry of Organic Compounds, First Edition; Eliel, E. L. & Wilen, S. H., Wiley, New Delhi, 2008.
  • Organic Chemistry, Vol. I, Sixth Edition; I.L. Finar; Pearson Education, New Delhi 2002.
  • Organic Chemistry, Sixth Edition; G. Marc Loudon, J. Parise; WH Freeman, New York, 2015.
  • Stereochemistry of Organic Compounds; Third Edition; D. Nasipuri; New Age International Publishers Pvt. Ltd, New Delhi, 2007.
  • Stereochemistry and Mechanism through solved Problems; Third Edition; P. S. Kalsi; New Age International Pvt. Ltd., New Delhi, 2004.

e-RESOURCES:

  • https://www.youtube.com/watch?v=yzfcrwJ37kI [2] (Unit IV & V)
  • https://epgp.inflibnet.ac.in/epgpdata/uploads/epgp_content/S000005CH/P000656/M026149/ET/1515563870CHE_P1_M8_etext.pdf [3] (Unit I)
  • https://epgp.inflibnet.ac.in/Home/ViewSubject?catid=13G8VouhmrFfuhs6rkiyTA== [4] (P-01) (Unit IV and V)
  • https://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/sterisom.htm#start [5] (Unit IV & V)
  • https://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/sterism2.htm#isom9 [6] (Unit IV & V)

 

Academic Year: 
2023-2024 [7]

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Source URL: https://chemistry.iisuniv.ac.in/courses/subjects/structure-reactivity-and-stereochemistry-organic-compounds-5

Links:
[1] https://chemistry.iisuniv.ac.in/courses/subjects/structure-reactivity-and-stereochemistry-organic-compounds-5
[2] https://www.youtube.com/watch?v=yzfcrwJ37kI
[3] https://epgp.inflibnet.ac.in/epgpdata/uploads/epgp_content/S000005CH/P000656/M026149/ET/1515563870CHE_P1_M8_etext.pdf
[4] https://epgp.inflibnet.ac.in/Home/ViewSubject?catid=13G8VouhmrFfuhs6rkiyTA==
[5] https://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/sterisom.htm#start
[6] https://www2.chemistry.msu.edu/faculty/reusch/VirtTxtJml/sterism2.htm#isom9
[7] https://chemistry.iisuniv.ac.in/academic-year/2023-2024