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Annexure ‘AAB-CD-01’

Course Title: ORGANIC CHEMISTRY I PG L T P/ SW/ TOTAL


Course Code: to be decided later S FW CREDIT UNITS
Credit Units: 04
3 0 0 2 4
Level: Post Graduate

Course Objectives:
To teach the fundamental concepts of organic chemistry and their applications, the present course includes four units, each of which is reasonably complete in
itself. The first unit discusses aromaticity and gives a detailed description of chirality. Special attention is paid to serve the needs of students in a way that will
enhance their comprehension of stereochemistry. The elucidation of reaction mechanism is one of the most important aspects of organic chemistry. A number
of electronic and steric factors that can influence the reactivity of a compound in a given situation have also been listed in the subsequent units.

Prerequisites: Student must have a basic Knowledge of Organic Chemistry.

Course Title Weightage


(%)
Module I Stereochemistry-I 30
 Stereoisomerism - concept of chirality and symmetry elements.
 Newman, Sawhorse and Fischer projection - formulae and inter conversions,
 Cahn - Ingold - Prelog system of nomenclature, Topicity and Prochirality: Topicity of ligands and faces. Enantiotopic
and diastereotopic atoms and groups.
 Molecules with more than one chiral centre - molecular chirality – atropisomerism, optical activity of biphenyls, allenes,
spiranes, cyclophanes, ansa compounds, trans-cyclooctene, helicenes, benzphenanthrenes.
 Configurational nomenclature; Stereochemistry of compounds containing nitrogen, sulphur and phosphorus.
 E - Z Nomenclature - Determination of configuration of the geometrical isomers. Geometrical isomerism of oximes of
carbonyl compounds.
 Conformational analysis of mono and substituted cycloalkanes, decalins. Effects of conformation on reactivity, strain
due to unavoidable crowding. Conformational analysis of sugars. Anomeric effect.

Module II Aromaticity, Reaction Intermediates and Kinetics 25


Aromaticity :
 Huckel's rule. Energy level of pi molecular orbitals and concept of aromaticity and anti-aromaticity.
 Chemistry of a few representative examples including fullerenes (C60), annulenes, and hetero annulenes
Determination of organic reaction mechanisms
 Kinetic and non-kinetic methods of determining reaction mechanism. Hammett and Taft Equation.
Reactive Intermediates
 Free radicals, carbenes, nitrenes, carbanions and carbocations - Formation, reactivity, stability and detection of reactive
intermediates

Module III Nucleophilic and Electrophilic Substitution reactions 25


Aliphatic Nucleophilic Substitution
 The SN2, SN1 mixed SN1 and SN2 and SET mechanism. Reactivity effects of substrate structure, attacking nucleophile,
leaving group and reaction medium.
 The neighboring group mechanism. Nucleophilic substitution at an allylic, aliphatic trigonal and a vinylic carbon.
Aromatic Nucleophilic Substitution:
 The SNAr and benzyne mechanism, Reactivity effect of substrate, structure, leaving group and attacking nucleophile.
Aliphatic Electrophilic Substitution:
 Bimolecular mechanisms - SE2 and SE1, The SE1 mechanism, electrophilic substitution accompanied by double bond
shifts.
 Effect of substrates, leaving groups and the solvent polarity on the reactivity.
Aromatic Electrophilic Substitution:
 The arenium ion mechanism, orientation and reactivity, energy profile diagrams.
 The ortho/ para ratio, orientation in other ring systems.
 Quantitative treatment of reactivity in substrates and electrophiles.

Module IV Free radical and Elimination reactions 20


Free Radical Reactions
 Types of free radical reactions, free radical substitution mechanism, mechanism at an aromatic substrate.
 Neighbouring group assistance. Reactivity for aliphatic and aromatic substrates at a bridgehead. The effect of solvents
on reactivity.
 Allylic halogenation (NBS), oxidation of aldehydes to carboxylic acids, auto-oxidation, coupling of alkynes and
arylation of aromatic compounds by diazonium salts, Sandmeyer reaction.
 Free radical rearrangement, Hunsdiecker reaction.
Elimination Reactions
 The E2, E1 and E1cb mechanisms, Orientation of the double bond.
 Reactivity-effects of substrate structures, attacking base, the leaving group and the medium.
 Mechanism and orientation in pyrolytic elimination.
Course Learning Outcomes

At the end of this course the student will be able to:


 Describe and distinguish the structural, geometric and optical isomers and apply knowledge of their structure.
 Predict the aromatic, non-aromatic and anti-aromatic nature of compounds
 Outline all the reactions with the reactant, reagents and products.
 Differentiate between substitution, addition and elimination reactions involving organic molecules.
 Propose and compose a mechanism of an organic reaction involving nucleophilic and electrophilic reagents on aliphatic or aromatic molecules.

Pedagogy for Course Delivery:


The course pedagogy will follow the four-quadrant approach i.e. using e-content like audio visual aids, video lectures, presentations, demonstration of stereo
chemical structures using molecular models, open source reference material, discussions on applications of topics covered. Assessment will be done through
assignments and quiz on topics covered after completion of modules.

List of Professional Skill Development Activities (PSDA):


i) Analysis of ongoing research on any one topic through research papers.
ii) Guest lecture by an expert.
iii) Group discussion

Assessment/ Examination Scheme:


Theory L/T (%) Lab/Practical/Studio (%)

100 % NA

Continuous Assessment/ Internal Lab/ practical End Term Examination


Assessment

40% NA 60%

Theory Assessment (L&T):

Continuous Assessment/Internal Assessment End Term Examination

Components (Drop CT HA1+ Quiz 1/ ATT EE


down) HA2 Quiz 2
Linkage of PSDA with Quiz 3
Internal Assessment
Component, if any

Weightage (%) 10 5+5 5+5+5 5 60

Abbreviations: CT – Class Test, Q- Quiz, HA- Home Assignment, ATT-Attendance, PSDA-Professional Skill Development Activities

Text Reading:
1. Advanced Organic Chemistry-Reactions, Mechanism and Structure, Jerry March,John Wiley.
2. Organic Chemistry, R.T. Morrison and R.N. Boyd, Prentice-Hall.
3. Reaction Mechanism in Organic Chemistry, S.M. Mukherji and S.P. Singh, Macmillan.
4. Organic Chemistry Vol. I & II , I. L. Finar , Longman .
References:
1. Advanced Organic Chemistry, F.A. Carey and R.J. Sundberg, Plenum.
2. A Guide Book to Mechanism in Organic Chemistry, Peter Sykes, Longman.
3. Stereochemistry of Organic Compounds, D.Nasipuri, New Age International.
4. Stereochemisty of Organic Compounds, P.S. Kalsi, New Age International

Additional Reading:
 Review articles

Any other Study Material: e-content and open source reference material available on Amizone
Mapping Continuous Evaluation components/PSDA with CLOs

Bloom’s Level > Remembering Understanding Applying Analysing Evaluating Creating

Course CLO1 CLO2 CLO3 CLO4 CLO5 CLO 5


Learning
Outcomes

Assessment
type/PSDA

Class Test √ √ √ √ √

Home √ √ √ √
Assignment
Quiz √ √ √ √

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