AC – 14/06/2018
Item No. 4.71
UNIVERSITY OF MUMBAI
Program : M .Sc.
( Choice Based Credit System )
Course : M.Sc. Organic Chemistry
Part – I
Syllabus for Semester III & IV
(To be implemented from the Academic year 2018 -2019 )
M.Sc. Organic Chemistry
Semester – III
Course Code: PSCHO301
Paper - I (Theoretical organic chemistry -I)
Unit 1 Organic reaction mechanisms [15L]
1.1 Organic reactive intermediates, methods of generation, structure, stability
and important reactions involving carbocations, nitrenes, carbenes, arynes
and ketenes . [5L]
1.2 Neighbouring group participation : Mechanism and effects of anchimeric
assistance, NGP by unshared/ lone pair electrons, π -electrons, aromatic
rings, σ -bonds with special reference to norbornyl and bicyclo[2.2.2]octyl
cation systems (formation of non -classical carbocation) [3L]
1.3 Role of FMOs in organic reactivity : Reactions involving hard and soft
electrophiles and nucleophiles, ambident nucleophiles, ambident
electrophiles, the α effect. [2L]
1.4 Pericyclic reactions: Classification of pericyclic reactions; thermal and
photochemical reactions. Three approaches:
Evidence for the concertedness of bond making and breaking
Symmetry -Allowed and Symmetry -Forbidden Reactions –
The Woodward -Hoffmann Rules -Class by Class
The generalised Woodward -Hoffmann Rule
Explanations for Woodward -Hoffmann Rules
The Aromatic Transition structures [Huckel and Mobius]
Frontier Orbitals
Correlation Diagrams, FMO and PMO approach
Molecular orbital symmetry, Frontier orbital of ethylene, 1,3 butadiene,
1,3,5 hexatriene and allyl system. [5L]
Unit 2 Pericyclic reactions [15L]
2.1 Cycloaddition reactions: Supra and antra facial additions, 4n and 4n+2
systems, 2+2 additions of ketenes . Diels -Alder reactions, 1, 3 -Dipolar
cycloaddition and cheletropic reactions, ene reaction, retro -Diels -Alder
reaction, regioselectivity, periselectivity, torquoselectivity, site selectivity
and effect of substituents in Diels -Alder reactions.
Other Cycloaddition Reactions - [4+6] Cycloadditions, Ketene
Cycloaddition, Allene Cycloadditions, Carbene Cycloaddition, Epoxidation
and Related Cycl oadditions.
Other Pericyclic reactions: Sigmatropic Rearrangements, Electrocyclic
Reactions, Alder ‘Ene’ Reactions. [7L]
2.2 Electrocyclic reactions: Conrotatory and disrotatary motions, 4n π and
(4n+2) π electron and allyl systems. [3L]
2.3 Sigmatropic rearrangements: H -shifts and C -shifts, supra and antarafacial
migrations, retention and inversion of configurations. Cope (including oxy -
Cope and aza -Cope) and Claisen rearrangements. Formation of Vitamin D
from 7 -dehydrocholest erol, synthesis of citral u sing pericyclic reaction,
conversion of Endiandric acid E to Endiandric acid A. [5L]
Unit 3 : Stereochemistry -I [15L]
3.1 Classification of point groups based on symmetry elements with examples
(nonmathematical treatment). [2L]
3.2 Conformational analysis of medium rings: Eight to ten membered rings and
their unusual properties , I-strain, transannular reactions. [3L]
3.3 Stereochemistry of fused ring and bridged ring compounds: decalins,
hydrindanes, perhydroanthracenes , steroids, and Bredt’s rule. [5L]
3.4 Anancomeric systems, Effect of conformation on reactivity of cyclohexane
derivatives in the following reactions (including mechanism): electrophilic
addition, elimination, molecular rearrangements, reduction of
cyclo hexanones (with LiAlH 4, selectride and MPV reduction) and
oxidation of cyclohexanols . [5L]
Unit 4 Photochemistry [15L]
4.1 Principles of photochemistry: quantum yield, electronic states and
transitions, selection rules, modes of dissipation of energy (Jablonski
diagram), electronic energy transfer: photosensitization and quenching
process. [3L]
4.2 Photochemistry of carbonyl compounds:π →՜π*, n →՜π* transitions,
Norrish - I and Norrish -II cleavages, Paterno -Buchi reaction.
Photoreduction , calculation of quantum yield, photochemistry of enones,
photochemical rearrangements of α, β -unsaturated ketones and
cyclohexadienones. Photo Fries rearrangement, Barton reaction. [8L]
4.3 Photochemistry of olefins: cis -trans isomerizations, dimerizatio ns, hydrogen
abstraction, addition and Di - π- methane rearrangement including aza -di- π
-methane. Photochemical Cross -Coupling of Alkenes, Photodimerisation of
alkenes . [2L]
4.4 Photochemistry of arenes : 1, 2- , 1, 3 - and 1, 4 - additions.
Photocycloadditions of aromatic Rings. [1L]
4.5 Singlet oxygen and photo -oxygenation reactions. Photochemically induced
Radical Reactions. Chemiluminescence.
REFERENCES:
[1L]
1 March’s Advanced Organic Chemistry, Jerry March, sixth edition,
2007, John Wiley and sons.
2 A guide to mechanism in Organic Chemistry, 6th edition, 2009,
Peter Sykes, Pearson education, New Delhi.
3 Advanced Organic Chemistry: Reaction Mechanisms, R. Bruckner,
Academic Press (2002).
4 Mechanism and theory in Organic Chemistry, T. H. Lowry and K.
C. Richardson, Harper and Row.
5 Organic Reaction Mechanism, 4th edition, V. K. Ahluvalia, R. K.
Parashar, Narosa Publication.
6 Reaction Mechanism in Organic Chemistry, S.M. Mukherji, S.P.
Singh, Macmillan Publishers, India.
7 Organic Chemistry, Part A and B, Fifth edition,2007, Francis A.
Carey and Richard J. Sundberg, Springer.
8 Carbenes, Nitrenes and Arynes. Von T. L. Gilchrist, C. W. Rees. Th.
Nelson and Sons Ltd., London 1969.
9 Organic reactive intermediates, Samuel P. MacManus, Academic
Press.
10 Organic Chemistry, J. Clayden, S. Warren, N. Greeves, P. Wothers,
1st Edition, Oxford University Press ( 2001).
11 Organic Chemistry, Seventh Edition, R.T. Morrison, R. N. Boyd &
S. K. Bhattacharjee, Pearson.Advanced Organic Chemistry: Reactions &
Mechanisms, second edition, B. Miller and R. Prasad, Pearson.
12 Organic reactions & their mechanisms, third revised edition, P.S.
Kalsi, New Age International Publishers.
13 Organic Chemistry: Structure and Function, P. Volhardt and N.
Schore, 5th Edition, 2012
14 Organic Chemistry, W. G. Solomons, C. B. Fryhle, , 9th Edition,
Wiley India Pvt. Ltd.,2009.
15 Pericyclic Reactions, S. Sankararaman, Wiley VCH, 2005.
16 Advanced organic chemistry, Jagdamba Singh L. D. S. Yadav,
Pragati Prakashan, 2011
17 Pericyclic reactions, Ian Fleming, Oxford university press, 1999.
18 Pericyclic reactions -A mechanistic approach, S. M. Mukherji,
Macmillan Co. of India 1979.
19 Organic chemistry, 8th edition, John McMurry
20 Modern methods of Organic Synthesis, 4th Edition W. C arruthers
and Iain Coldham, Cambridge University Press 2004
21 Modern physical chemistry, Eric V Anslyn, Dennis A. Dougherty,
University science books,2006
22 Physical Organic Chemistry, N. S. Isaacs, ELBS/Longman
23 Stereochemistry of Carbon Compounds: Principles and
Applications, D, Nasipuri, 3rd edition, New Age International Ltd.
24 Stereochemistry of Organic Compounds, Ernest L. Eliel and Samuel
H. Wilen, Wiley -India edit
25 Stereochemistry, P. S. Kalsi, 4th edition, New Age International Ltd
26 Organic Stereochemistry, M. J. T. Robinson, Oxford University
Press, New Delhi, India edition, 2005
27 Bioorganic, Bioinorganic and Supramolecular chemistry, P.S. Kalsi
and J.P. Kalsi. New Age International Publishers
28 Supramolecular Chemistry; Concepts and Perspectives, J. M. Lehn,
VCH.
29 Crown ethers and analogous compounds, M. Hiraoka, Elsevier,
1992.
30 Large ring compounds, J.A.Semlyen, Wiley -VCH, 1997.
31 Fundamentals of Photochemistry, K. K. Rohtagi -Mukherji, Wiley -
Eastern
32 Essentials of Molecular Photochemistry, A. Gilbert and J. Baggott,
Blackwell Sciertific Publication.
33 Molecular Photochemistry, N. J. Turro, W. A. Benjamin.
34 Introductory Photochemistry, A. Cox and T. Camp, McGraw -Hill
35 Photochemistry, R. P. Kunda ll and A. Gilbert, Thomson Nelson.
36 Organic Photochemistry, J. Coxon and B. Halton, Cambridge
University Press.
37 Molecular Orbitals and Organic Chemical Reactions by Ian Fleming
(Wiley – A john Wiley and Sons, Ltd., Publication)
Course Code: PS CHO302
Paper -II
Synthetic Organic Chemistry -I
Unit 1: Name reactions with mechanism and application [15L]
1.1 Mukaiyama esterification, Mitsonobu reaction, Darzen’s Glycidic Ester
syntheis, Ritter reaction, Yamaguchi esterification, Peterson olefination. [5L]
1.2 Domino reactions : Characteristics; Nazerov cyclization [3L]
1.3 Multicomponent reactions : Strecker Synthesis, Ugi 4CC, Biginelli
synthesis, Hantzsch synthesis, Pictet -Spengler synthesis [5L]
1.4 Click Reactions : Characteristics; Huisgen 1,3-Dipolar Cycloaddition [2L]
Unit 2: Radicals in organic synthesis [15L]
2.1 Introduction: Generation, stability, reactivity and structural and
stereochemical properties of free radicals, Persistent and charged radicals,
Electrophilic and nucleophilic radicals. [3L]
2.2 Radical Initiators : azobisisobutyronitrile (AIBN) and dibenzoyl peroxide. [1L]
2.3 Characteristic reactions - Free radical substitu tion, addition to multiple
bonds. Radical chain reactions, Radical halogenation of hydrocarbons
(Regioselectivity),radical cyclizations, autoxidations: synthesis of cumene
hydroperoxide from cumene. [4L]
2.4 Radicals in synthesis : Inter and intra molecular C -C bond formation via
mercuric hydride, tin hydride, thiol donors. Cleavage of C -X, C -Sn, C -Co,
C-S, O -O bonds. Oxidative coupling, C -C bond formation in aromatics:
SRNAr reactions. [4L]
2.5 Hunsdiecker reaction, Pinacol coupling, McMurry coupling, Sandmeyer
reaction, Acyloin condensation. [3L]
Unit 3: Enamines, Ylides and α-C-H functionalization [15]
3.1 Enamines: Generation & application in organic synthesis with mechanistic
pathways, Stork enamine reaction. Reactivity, comparison between
enamines and enolates. Synthetic reactions of enamines including
asymmetric reactions of chiral enamines derived from chiral secondary
amine s. [4L]
3.2 Phosphorus, Sulfur and Nitrogen Ylides: Preparation and their synthetic
applications along with their stereochemical aspects. Wittig reaction,
Horner -Wadsworth -Emmons Reaction, Barton -Kellogg olefination. [6L]
3.3 α-C-H functionalization: By nitro, sulfoxide, sulfone and phosphonate
groups: generation of carbanions by strong bases (LDA/n -butyl lithium) and
applications in C -C bond formation. Bamford -Stevens reaction, Julia
olefination and its modification, Seyferth –Gilbert homologation, St even’s
rearrangement. [5L]
Unit 4: Metals / Non -metals in organic synthesis [15]
4.1 Mercury in organic synthesis: Mechanism and regiochemistry of
oxymercuration and demercuration of alkenes, mercuration of aromatics,
transformation of aryl mercurials to aryl halides. Organomercurials as
carbene transfer reagents . [3L]
4.2 Organoboron compounds: Mechanism and regiochemistry of
hydroboration of alkenes and alkynes, asymmetric hydroboration using
chiral boron reagents, 9 -BBN hydroboration, oxazaborolidine (CBS
catalyst) and functional group reduction by diborane . [3L]
4.3 Organosilicons: Salient features of silicon governing the reactivity of
organosilicons, preparation and important bond -forming reactions of alkyl
silanes, alkenyl silanes, aryl silanes and allyl silanes. β -silyl cations as
intermediates. Iodotrimethylsilane in organic synthesis . [3L]
4.4 Silyl enol ethers : Application: As nucleophiles (Michael reaction,
Mukaiyama aldol reaction), in ring contraction reactions . [2L]
4.5 Organotin compounds : Preparation of alkenyl and allyl tin compounds;
application in C -C bond formation, in replacement of halogen by H at the
same C atom . [2L]
4.6 Selenium in organic synthesis: Preparation of selenols/selenoxide,
selenoxide elimination to create unsaturation, selenoxide and seleno acetals
as α-C-H activating groups
References [2L]
Advanced Organic Chemistry, Part A and Part B: Reaction and
Synthesis, Francis A. Carey, Richard J. Sundberg, 5th Edition,
Springer Verlag
Modern Methods of Organic Synthesis, 4th Edition, W. Carruthers
and Iain Coldham, Cambridge University Press, 2004.
Chem.Rev. 2002, 102, 2227 -2302, Rare Earth Metal Triflates in
Organic Synthesis, S. Kobayashi, M. Sugiura, H. Kitagawa, and
W.W.L. Lam.
Organic Chemistry, Clayden Greeves Warren and Wothers,
Oxford Press (2001).
Moder Organic Synthesis: An Introduction, G.S. Zweifel and
M.H. Nantz, W.H. Freeman and Company, (2007).
Advanced Organic Chemistry: Reaction Mechanism, R.
Bruckner, Academic Press (2002).
Principles of Organic Synthesis, R.O.C. Norman & J. M. Coxon,
3rd Edn., Nelson Thornes
Organic Chemistry, 7th Edn, R. T .Morrison, R. N. Boyd, & S. K.
Bhattacharjee, Pearson
Strategic Applications of Name Reactions in Organic Synthesis ,
L. Kurti & B. Czako (2005), Elsevier Academic Press
Advanced Organic Chemistry: Reactions & Mechanisms, 2nd
Edn., B. Miller & R. Prasad, Pearson
Organic reactions and their mechanisms, 3rd revisededition, P.S.
Kalsi, New Age International Publishers
Organic Synthesi s: The Disconnection Approach, Stuart Warren,
John Wiley & Sons, 2004
Name Reactions and Reagents in Organic Synthesis, 2nd Edn.,
Bradford P. Mundy, Michael G. Ellard, and Frank Favoloro, Jr.,
Wiley -Interscience
Name Reactions, Jie Jack Lie, 3rd Edn., Spri nger
Organic Electrochemistry, H. Lund, and M. Baizer, 3rd Edn.,
Marcel Dekker.
Course Code: PSCHO303
Paper -III
Natural products and Spectroscopy
Unit 1: Natural products -I [15L]
1.1 Carbohydrates: Introduction to naturally occurring sugars: Deoxysugars,
aminosugars, branched sugars. Structure elucidation of lactose and D -
glucosamine (synthesis not expected).Structural features and applications of
inositol, starch, cellulose, chitin and heparin . [5L]
1.2 Natural pigments: General structural features, occurrence, biological
importance and applications of: carotenoids, anthocyanins, quinones,
flavones, pterins and porphyrins (chlorophyll). Structure elucidation of β -
carotene and Cyanin (with synthesis). Synthesis of ubiquinone from 3, 4, 5 -
trimethoxyacetophenone. [5L]
1.3 Insect pheromones: General structural features and importance. Types of
pheromones (aggregation, alarm, releaser, primer, territorial, trail, sex
pheromones etc.), advantage of pheromones over conventional pesticides.
Synthe sis of bombykol from acetylene, disparlure from 6 -methylhept -1-ene,
grandisol from 2 -methyl -1, 3-butadiene . [3L]
1.4 Alkaloids: Occurrence and physiological importance of morphine and
atropine . Structure elucidation, spe ctral data and synthesis of coniine. [2L]
Unit 2: Natural products -II [15L]
2.1 Multi -step synthesis of natural products: Synthesis of the following
natural products with special reference to reagents used, stereochemistry
and functional group transformations: [8L]
a) Woodward synthesis of Reserpine from benzoquinone
b) Corey synthesis of Longifoline from resorcinol
c) Gilbert -Stork synthesis of Griseofulvin from phloroglucinol
d) Corey’s Synthesis of Caryophyllene from 2 -Cyclohexenone and
Isobutylene
e) Synthesis of Juvabione from Limonene
f) Synthesis of Taxol.
2.2 Prostaglandins: Classification, general structure and biological
importance. Structure elucidation of PGE 1. [2L]
2.3 Lipids: Classification, role of lipids, Fatty acids and glycerol derived from
oils and fats . [2L]
2.4 Insect growth regulators: General idea, structures of JH 2 and JH 3 . [1L]
2.5 Plant growth regulators: Structural features and applications of arylacetic
acids, gibberellic acids and triacontanol. Synthesis of triacontanol (synthesis
of stearyl magnesium bromide and 12 -bromo -1-
tetrahydropyranyloxydodecane expected). [2L]
Unit 3: Advanced spectroscopic techniques -I [15L]
3.1 Proton NMR spectroscopy: Recapitulation, chemical and magnetic
equivalence of protons, First order, second order, Spin system notations
(A2, AB, AX, AB 2, AX 2, AMX and A 2B2-A2X2 spin systems with suitable
examples). Long range coupling (Allylic coupling, ‘W’ coupling and
Coupling in aromatic and heteroaromatic systems), Temperature effects,
Simplif ication of complex spectra, nuclear magnetic double resonance,
chemical shift reagents. [7L]
3.2 13C –NMR spectroscopy: Recapitulation, equivalent and non -equivalent
carbons (examples of aliphatic and aromatic compounds), 13C- chemical
shifts, calculation of 13C- chemical shifts of aromatic carbons, heteronuclear
coupling of carbon to 19F and 31P. [4L]
3.3 Spectral problems based on UV, IR, 1HNMR and 13CNMR and Mass
spectroscopy . [4L]
Unit 4: Advanced spectroscopic techniques -II [15L]
4.1 Advanced NMR techniques: DEPT experiment, determining number of
attached hydrogens (Methyl/methylene/methine and quaternary carbons),
two dimensional spectroscopic techniques, COSY and HETCOR spectra,
NOE and NOESY techniques. [10L]
4.2 Spectral problems based on UV, IR, 1HNMR, 13CNMR (Including 2D
technique) and Mass spectroscopy
REFERENCES: [5L]
1. Natural product chemistry, A mechanistic, biosynthetic and
ecological approach, Kurt B.G. Torssell, Apotekarsocieteten –
Swedish Pharmaceutical Press.
2. Natural products chemistry and applications, Sujata V. Bhat, B.A.
Nagasampagi and S. Meenakshi, Narosa Publishing House, 2011.
3. Organic Chemistry Natural Products Volume -II, O. P. Agarwal,
Krishna Prakashan , 2011.
4. Chemistry of natural products, F. F. Bentley and F. R. Dollish, 1974
5. Natural Product Chemistry Vol.1 and 2, K. Nakanishi J. Goto. S.Ito
Majori and S. Nozoo, Academic Press, 1974.
6. Chemistry of natural products, V.K. Ahluwalia, Vishal Publishing
Co. 2008.
7. Heterocyclic chemistry, 3rd edition, Thomas L. Gilchrist, Pearson
Education, 2007.
8. Heterocyclic Chemistry, Synthesis, Reactions and Mechanisms , R.
K. Bansal, Wiley
Eastern Ltd., 1990.
9. Heterocyclic Chemistry , J. A. Joule and G. F. Smith , ELBS, 2nd
edition, 1982.
10. The Conformational Analysis of Heterocyclic Compounds , F.G.
Riddell, Academic Press,1980.
11. Principles of Modern Heterocyclic Chemistry , L.A. Paquette, W.B.
Benjamin, Inc., 1978.
12. An Introduction to the Chemistry of Heterocyclic Compounds , 2nd
edition, B.M. Acheson, 1975.
13. Natural Products: Chemistry and Biological Significance
Interscience, J. Mann, R.S.Davidson, J.B.Hobbs, D.V. Banthrope
and J. B. Harborne, Longman,Essex, 1994.
14. Organic Chemistry, Vol 2, I.L. Finar, ELBS, 6th edition, Pearson.
15. Stereoselective Synthesis: A Practical Approach, M. Nogradi,
Wiley -VCH, 1995.
16. Rodd’s Chemistry of Carbon Compounds, Ed. S. Coffey, Elsevier.
17. Chemistry, Biological and Pharmacological Properties of Medicinal
Plants from the Americas, Ed. Kurt Hostettmann, M.P. Gupta and A.
Marston, Harwood Academic Publishers.
18. Introduction to Flavonoids, B.A. Bohm, Harwood Academic
Publishers, 1998.
19. New Trends i n Natural Product Chemistry, Atta -ur-Rahman and
M.I. Choudhary, Harwood Academic Publishers, 1998.
20. Insecticides of Natural Origin, Sukh Dev, Harwood Academic
Publishers.
21. Total. Synthesis of Longifolene, J. Am. Chem. Soc ., E. J. Corey, M.
Ohno, R. B. Mitra, and P. A. Vatakencherry. 1964, 86, 478.
22. Total. Synthesis of Longifolene, J. Am. Chem. Soc . 1961 , 83, 1251 .
23. The structure and total synthesis of 5 -Vetivone, J. A. Marshall
and P. C. Johnson, J. Org. Chem., 35, 192 (1970).
24. Total synthesis of spirovetivanes, J. Am. Chem. Soc. 1967, 89,
2750.
25. The Total Synthesis of Reserpine, Woodward, R. B.; Bader, F. E.;
Bickel, H., Frey, A. J.; Kierstead, R. W. Tetrahedron 1958 , 2, 1-57.
26. Total synthesis of Griseofulvin, Stork, G.; Tomasz, M. J. Am.
Chem. Soc. 1962, 84, 310.
27. Synthesis of (±) -4-demethoxydaunomycinone, A. V. Rama Rao ,
G. Venkatswamy , S. M. Javeed M. , V. H. Deshpande , B.
Ramamohan Rao , J. Org. Chem. , 1983, 48 (9), 1552.
28. The Alkaloids, The fundamental Chemistry A biogenetic approach,
Marcel Dekker Inc. New York, 1979.
29. Comprehensive Organic Chemistry by Barton and Olis, Pergamon
Press, Oxford, 1979.
30. Medicinal Natural Products, a Biosynt hetic Approach, Derick Paul,
John Wiley and Sons, 2002.
31. Biosynthesis of Natural Products, Mannitto Paolo, Ellis Horwoocl
Limited, 1981.
32. Selected Organic synthesis, Ian Fleming, John Wiley and Sons,
1973.
33. Total synthesis of Natural Products, J. Apsimon, Jo hn Wiley
and Sons.
34. The Logic of Chemical Synthesis, E. J. Corey and Xue -Min Cheng,
Wiley Interscience.
35. Classics in Total Synthesis , K. C. Nicolaou and E. J. Sorensen,
Weinhem: VCH, 1996.
36. Spectroscopy of Organic compounds, P.S. Kalsi, New Age
International Pub. Ltd. And Wiley Eastern Ltd., Second edition,
1995.
37. Applications of Absorption Spectroscopy of Organic compounds, J.
R. Dyer, Prentice Hall of India, 1987.
38. Spectrometric Identification of Organic compounds, R.M.
Silverstein and others, John Wiley and Sons Inc., 5th ed., 1991
39. Absorption spectroscopy of organic Molecules, V.M. Parikh, 1974.
40. Spectroscopic methods in organic chemistry, Williams and Fleming,
Tata McGraw Hill, 4th ed, 1989.
41. Organic spectroscopy, William Kemp, ELBS, 3rd ed., 1987.
42. Organic structures from spectra, L. D. Field , S. Sternhell , John R.
Kalman , Wiley, 4th ed., 3122.
43. Introduction to spectroscopy, Donald L. Pavia , Gary M. Lampman ,
George S. Kriz , James R. Vyvyan, 4th ed., 2009.
44. Organic spectroscopic structure determination : a problem -based
learning approach Douglass F. Taber , Oxford University Press, 17-
Sep-2007 .
45. Organic Spectroscopy : Principles And Applications, Jag Mohan ,
Alpha Science International Ltd., 30-Mar-2004
46. Alkaloids,V.K. Ahulu walia,Ane Books Pvt.Ltd.
47. Biotransformations in Organic Chemistry, 5thEdition, Kurt Faber,
Springer
48. Structure Determination of Organic Compounds, EPretsch, P.
Buhlmann, C.Affolter, Springer
Course Code: PSCHO EC-I 304
Paper -IV
Medicinal , Biogenesis and green chemistry
Unit 1: Drug discovery, design and development [15L]
1.1 Introduction, important terms used in medicinal chemistry: receptor,
therapeutic index, bioavailability, drug assay and drug potency. General
idea of factors affecting bioactivity: Resonance, inductive effect,
bioisosterism, spatial considerations. Basic p harmacokinetics: drug
absorption, distribution, metabolism (biotransformation) and elimination.
Physical and chemical parameters like solubility, lipophilicity, ionization,
pH, redox potential, H -bonding, partition coefficient and isomerism in drug
distrib ution and drug -receptor binding. [7]
1.2 Procedures in drug design: Drug discovery without a lead: Penicillin,
Librium. Lead discovery: random screening, non -random (or targeted)
screening. Lead modification: Identification of the pharmacophore,
Functiona l group modification. Structure -activity relationship, Structure
modification to increase potency and therapeutic index: Homologation,
chain branching, ring -chain transformation, bioisosterism, combinatiorial
synthesis (basic idea). [8L]
Unit 2 : Drug design, development and synthesis [15L]
2.1 Introduction to quantitative structure activity relationship studies. QSAR
parameters: - steric effects: The Taft and other equations; Methods used to
correlate regression parameters with biological activity: Hansch analysis - A
linear multiple regression analysis. [5L]
2.2 Introduction to modern methods of drug design and synthesis - computer -
aided molecular graphics based drug design, drug design via enzyme
inhibition (reversible and irreversible), bioinformatics and drug design. [3L]
2.3 Concept of prodrugs and soft drugs. (a) Prodrugs: Prodrug design, types of
prodrugs, functional groups in prodrugs, advantages of prodrug use. (b) Soft
drugs: co ncept and properties. [3L]
2.4 Synthesis and application of the following dru gs: Fluoxetine, cetrizine,
esomeprazole, fluconazole, zidovudine, methotrexate, diclofenac, labetalol,
fenofibrate. [4L]
Unit 3: Biogenesis and biosynthesis of natural products [15L]
3.1 Primary and secondary metabolites and the building blocks, general
pathway of amino acid biosynthesis. [3L]
3.2 Acetate pathway: Biosynthesis of malonylCoA , saturated fatty acids,
prostaglandins from arachidonic acid, aromatic polyketides. [4L]
3.3 Shikimic Acid pathway: Biosynthesis of shikimic acid, aromatic amino
acids, cinnamic acid and its derivatives, lignin and lignans , benzoic acid and
its derivatives, flavonoids and isofalvonoids. [4L]
3.4 Mevalo nate pathway: Biosynthesis of me valonic acid, monoterpenes –
geranyl cation and its derivatives, sesquiterpenes – farnesyl cation and its
derivatives and diterpenes. [4L]
Unit 4: Green chemistry [15L]
4.1 Introduction, basic principles of green chemistry. Designing a green
synthesis: Green starting materials, green reagents, green solvents and
reaction conditions, green catalysts . [1L]
4.2 Use of the following in green synthesis with suitable examples: [9L]
a) Green reagents: dimethylcarbonate, polymer supported reagents.
b) Green catalysts: Acid catalysts, oxidation catalysts, basic catalysts, phase
transfer catalysts [Aliquat 336, benzyltrimethyl ammonium chloride
(TMBA), Tetra -n-butyl ammonium chloride, crown ethers], biocatalysts.
c) Green solvents: water, ionic liquids, deep eutectic solvents, su percritical
carbon dioxide.
d) Solid state reactions: solid phase synthesis, solid supported synthesis
e) Microwave assisted synthesis: reactions in water, reactions in organic
solvents, solvent free reactions.
f) Ultrasound assisted reactions.
4.3 Comparison of traditional processes versus green processes in the syntheses
of ibuprofen, adipic acid, 4 -aminodiphenylamine, p -bromotoluene and
benzimidazole. [3L]
4.4 Green Cataysts : Nanocatalyst, Types of nanoctalysts , Advantages and
Disadvantages of Nanocatalysts, Idea of Magnetically separable
nanocatalysts.
REFERENCES: [2L]
1. Nelson, D. L, and Cox, M. M, (2008) Lehninger principles of
Biochemistry 5th Edition, W. H. Freeman and Company, NY., USA.
2. Stryer, Lubert; Biochemistry; W. H. Freeman publishers .
3. Voet, D. and J. G. Voet (2004) Biochemistry, 3rd Edition, John Wiley &
sons, Inc. USA.
4. Zubay, Goffrey L; Biochemistry; Wm C. Brown publishers.
5. V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara and J -M
Basset, Chem. Rev. 2011, 111, 3036 -3075;
6. R. B. Nasir Baig and R. S.Varma, Chem. Comm., 2013, 49, 752 -770;
7. M. B. Gawande, A. K. Rathi, P. S. Varma, Appl. Sci., 2013, 3, 656 -674;
8. J. Govan and Y. K. Gun’ko, Nanomaterials, 2014, 4, 222 -214.
9. K. Philipp ot and P. Serp, Nanomaterials in catalysis, First Edition.
Edited by P. Serp and K. Philippot; 2013 Wiley –VCH Verlag GmbH &
Co. K GaA
10. D. Astruc, Nanomaterials and Catalysis, Wiley -VCH Verlag GmbH &
Co. KGaA, 2008, 1 -48;
11. C. N. R. Roa, A. Muller and A. K. C heetham, The chemistry of
Nanomaterials, Wiley -VCH Verlag GmbH & Co. KGaA, 2005, 1 -11;
12. The organic chemistry of drug design and drug action, Richard B.
Silverman, 2nd edition, Academic Press
13. Medicinal chemistry, D.Sriram and P. Yogeeswari, 2nd edition, Pe arson
14. An introduction to drug design -S. S. Pandeya and J. R. Dimmock (New
age international)
15. Burger’s medicinal chemistry and drug discovery. by Manfred E. Wolf
16. Introduction to Medicinal chemistry. by Graham Patrick
17. Medicinal chemistry -William O. Foye
18. T. B . of Organic medicinal and pharmaceutical chemistry -Wilson and
Gisvold’s (Ed. Robert F. Dorge)
19. An introduction to medicinal chemistry -Graham L. Patrick, OUP
Oxford, 2009.
20. Principles of medicinal chemistry (Vol. I and II) -S. S. Kadam, K. R.
Mahadik and K.G. Bothara , Nirali prakashan.
21. Medicinal chemistry (Vol. I and II) -Burger
22. Strategies for organic drug synthesis and design - D. Lednicer Wiley
23. Pharmacological basis of therapeutics -Goodman and Gilman’s
(McGraw Hill)
24. Enzyme catalysis in organic synthesis, 3r d edition. Edited by Karlheinz
Drauz, Harold Groger, and Oliver May, Wiley -VCH Verlag GmbH &
Co KgaA, 2012.
25. Biochemistry, Dr U Satyanarayan and Dr U Chakrapani, Books and
Allied (P) Ltd.
26. Bioorganic, Bioinorganic and Supramolecular chemistry, P.S. Kalsi an d
J.P. Kalsi. New Age International Publishers
27. The Organic Chemistry of Enzyme -Catalysed Reactions, Academic
Press, By Richard B. Silverman
28. Enzymes: Practical Introduction to structure, mechanism and data
analysis, By Robert A. Copeland, Wiley -VCH, Inc.
29. The Organic Chemistry of Biological Pathways By John McMurry,
Tadhg Begley by Robert and company publishers
30. Bioorganic Chemistry - A practical approach to Enzyme action, H.
Dugas and C. Penny. Springer Verlag, 1931
31. Biochemistry: The chemical reactions in living cells, by E. Metzler.
Academic Press.
32. Concepts in biotechnology by D. Balasubrarnanian & others
33. Principals of biochemistry by Horton & others.
34. Bioorganic chemistry - A chemical approach to enzyme action by
Herman Dugas and Christopher Penney.
35. Medicinal Natural Products: A Biosynthetic Approach by Paul M.
Dewick. 3rd Edition, Wiley.
36. Natural product chemistry, A mechanistic, biosynthetic and ecological
approach, Kurt B. G. Torssell, Apotekarsocieteten – Swedish
pharmaceutical press.
37. Natural pr oducts Chemistry and applications, Sujata V Bhat, B.A.
Nagasampagi and S. Meenakshi, Narosa Publishing House .
38. Natural Products Volume - 2, By O. P. Agarwal .
39. Chemistry of Natural Products, F. F. Bentley and F. R. Dollish, 1974 .
40. Natural Product Chemistry V ol.1 and 2, K. Nakanishi J. Goto. S.Ito
Majori and S. Nozoo, Academic Press, 1974.
41. Chemistry of natural products, V.K. Ahluwalia, Vishal Publishing Co.
42. Green Chemistry: An Introductory Text, 2nd Edition, Published by
Royal Society of Chemistry, Authored by Mike Lancater .
43. Organic synthesis in water. By Paul A. Grieco, Blackie.
44. Green chemistry, Theory and Practical, Paul T. Anastas and John C.
Warner.
45. New trends in green chemistry By V. K. Ahulwalia and M. Kidwai, 2nd
edition, Anamaya Publishers, New Del hi.
46. An introduction to green chemistry, V. Kumar, Vishal Publishing Co .
47. Organic synthesis: Special techniques. V.K.Ahulwalia and Renu
Aggarwal.
Course Code: PSCHO EC-II 304
Paper -IV
Bioorganic chemistry
Unit 1: Biomolecules -I [15L]
1.1 Amino acids, peptides and proteins: Chemical and enzymatic hydrolysis of
proteins to peptides, amino acid sequencing. Secondary structure of
proteins, forces responsible for holding of secondary structures, α - helix, β -
sheets, super secondary structure. Te rtiary structure of protein: folding and
domain structure. Quaternary structure. [2L]
1.2 Nucleic acids: Structure and function of physiologically important
nucleotides (c -AMP, ADP, ATP) and nucleic acids (DNA and RNA),
replication, genetic code, protein biosynthesis, mutation. [3L]
1.3 Structure: Purine & pyrimidine bases, ribose, deoxyribose, nucleosides and
nucleotides (ATP, CTP, GTP, TTP, UTP) formation of polynucleotides
strand with its shorthand representation . [3L]
1.4 RNAs (various types in prokaryotes and eukaryotes) m - RNA and r - RNA
– general account , t - RNA -clover leaf model, Ribozymes . [2L]
1.5 DNA: Physical properties – Effect of heat on physical properties of DNA
(Viscosity, buoyant density and UV absorption ), Hypochromism,
Hyperchromism and Denaturation of DNA. Reactions of nucleic acids (with
DPA and Orcinol). [2L]
1.6 Chemical synthesis of oligonucleotides: Phosphodiester, Phosphotriester, [3L]
Phosphoramidite and H - phosphonate methods including solid phase
approach.
Unit 2: Biomolecules -II [15L]
2.1 Chemistry of enzymes: Introduction, nomenclature, classes and general
types of reactions catalyzed by enzymes. Properties of enzymes: a) enzyme
efficiency/ catalytic power b) enzyme specificity; Fischer’s ‘lock and key’
and Koshland ‘induced fit’ hypothesi s. Concept and identification of active
site. [6L]
2.2 Factors affecting enzyme kinetics: Substrate concentration, enzyme
concentration, temperature, pH, product concentration etc. Reversible and
irreversible inhibition. [4L]
2.3 Mechanism of enzyme ac tion: transition -state theory, orientation and steric
effect, acid -base catalysis, covalent catalysis, strain or distortion.
Mechanism of chymotrypsin catalyzed hydrolysis of a peptide bond. [5L]
Unit 3: Biomolecules - III [15L]
3.1 Chemistry of coenzymes. Structure, mechanism of action and bio -modeling
studies of the following coenzymes: nicotinamide adenine dinucleotide,
flavin adenine dinucleotide, thiamine pyrophosphate, pyridoxal phosphate,
Vitamin B12, biotin, lipoic acid, Coenzyme A. [12L]
3.2 Oxidative phosphorylation, chemiosmosis, rotary model for ATP synthesis
and role of cytochrome in oxy gen activation. [3L]
Unit 4: Biomolecules – IV [15L]
4.1 Role of main enzymes involved in the synthesis and breakdown of
glycogen. [2L]
4.2 Enzyme catalyzed organic reactions: Hydrolysis, hydroxylation, oxidation
and reduction. [6L]
4.3 Enzymes in organic synthesis. Fermentation: Production of drugs/drug
intermediates by fermentation. Production of chiral hydroxy acids,
vitamins, amino acids, β -lactam antibiotics. Synthesis of chemicals via
microbial transformation, synthesis of L -ephedrine. Chemical processes
with isolated enzymes in free form (hydrocyanation of m -
phenoxybenzaldehyde) and immobilized form (produc tion of 6 -
aminopenicillanic acid). [7L]
REFERENCES:
1. Nelson, D. L, and Cox, M. M, (2008) Lehninger principles of
Biochemistry 5th Edition, W. H. Freeman and Company, NY., USA.
2. Stryer, Lubert; Biochemistry; W. H. Freeman publishers .
3. Voet, D. and J. G. Voet (2004) Biochemistry, 3rd Edition, John Wiley &
sons, Inc. USA.
4. Zubay, Goffrey L; Biochemistry; Wm C. Brown publishers.
5. V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara and J -M
Basset, Chem. Rev. 2011, 111, 3036 -3075;
6. R. B. Nasir Baig and R. S .Varma, Chem. Comm., 2013, 49, 752 -770;
7. M. B. Gawande, A. K. Rathi, P. S. Varma, Appl. Sci., 2013, 3, 656 -674;
8. J. Govan and Y. K. Gun’ko, Nanomaterials, 2014, 4, 222 -214.
9. K. Philippot and P. Serp, Nanomaterials in catalysis, First Edition.
Edited by P. Ser p and K. Philippot; 2013 Wiley –VCH Verlag GmbH &
Co. K GaA
10. D. Astruc, Nanomaterials and Catalysis, Wiley -VCH Verlag GmbH &
Co. KGaA, 2008, 1 -48;
11. C. N. R. Roa, A. Muller and A. K. Cheetham, The chemistry of
Nanomaterials, Wiley -VCH Verlag GmbH & Co. KGaA, 2005, 1 -11;
12. The organic chemistry of drug design and drug action, Richard B.
Silverman, 2nd edition, Academic Press
13. Medicinal chemistry, D.Sriram and P. Yogeeswari, 2nd edition, Pearson
14. An introduction to drug design -S. S. Pandeya and J. R. Dimmock (New
age international)
15. Burger’s medicinal chemistry and drug discovery. by Manfred E. Wolf
16. Introduction to Medicinal chemistry. by Graham Patrick
17. Medicinal chemistry -William O. Foye
18. T. B. of Organic medicinal and pharmaceutical chemistry -Wilson and
Gisvold’s (E d. Robert F. Dorge)
19. An introduction to medicinal chemistry -Graham L. Patrick, OUP
Oxford, 2009.
20. Principles of medicinal chemistry (Vol. I and II) -S. S. Kadam, K. R.
Mahadik and K.G. Bothara , Nirali prakashan.
21. Medicinal chemistry (Vol. I and II) -Burger
22. Strategies for organic drug synthesis and design - D. Lednicer Wiley
23. Pharmacological basis of therapeutics -Goodman and Gilman’s
(McGraw Hill)
24. Enzyme catalysis in organic synthesis, 3rd edition. Edited by Karlheinz
Drauz, Harold Groger , and Oliver May, Wiley -VCH Verlag GmbH &
Co KgaA, 2012.
25. Biochemistry, Dr U Satyanarayan and Dr U Chakrapani, Books and
Allied (P) Ltd.
26. Bioorganic, Bioinorganic and Supramolecular chemistry, P.S. Kalsi and
J.P. Kalsi. New Age International Publishers
27. The Organic Chemistry of Enzyme -Catalysed Reactions, Academic
Press, By Richard B. Silverman
28. Enzymes: Practical Introduction to structure, mechanism and data
analysis, By Robert A. Copeland, Wiley -VCH, Inc.
29. The Organic Chemistry of Biological Pathways By J ohn McMurry,
Tadhg Begley by Robert and company publishers
30. Bioorganic Chemistry - A practical approach to Enzyme action, H.
Dugas and C. Penny. Springer Verlag, 1931
31. Biochemistry: The chemical reactions in living cells, by E. Metzler.
Academic Press.
32. Concepts in biotechnology by D. Balasubrarnanian & others
33. Principals of biochemistry by Horton & others.
34. Bioorganic chemistry - A chemical approach to enzyme action by
Herman Dugas and Christopher Penney.
35. Medicinal Natural Products: A Biosynthetic Approach by Paul M.
Dewick. 3rd Edition, Wiley.
36. Natural product chemistry, A mechanistic, biosynthetic and ecological
approach, Kurt B. G. Torssell, Apotekarsocieteten – Swedish
pharmaceutical press.
37. Natural products Chemistry and applications, Sujata V Bhat, B. A.
Nagasampagi and S. Meenakshi, Narosa Publishing House .
38. Natural Products Volume - 2, By O. P. Agarwal .
39. Chemistry of Natural Products, F. F. Bentley and F. R. Dollish, 1974 .
40. Natural Product Chemistry Vol.1 and 2, K. Nakanishi J. Goto. S.Ito
Majori and S . Nozoo, Academic Press, 1974.
41. Chemistry of natural products, V.K. Ahluwalia, Vishal Publishing Co.
42. Green Chemistry: An Introductory Text, 2nd Edition, Published by
Royal Society of Chemistry, Authored by Mike Lancater .
43. Organic synthesis in water. By Pa ul A. Grieco, Blackie.
44. Green chemistry, Theory and Practical, Paul T. Anastas and John C.
Warner.
45. New trends in green chemistry By V. K. Ahulwalia and M. Kidwai, 2nd
edition, Anamaya Publishers, New Delhi .
46. An introduction to green chemistry, V. Kumar, Vishal Publishing Co .
47. Organic synthesis: Special techniques. V.K.Ahulwalia and Renu
Aggarwal.
Semester III: Practicals
Course code: PSCHO3P1
Separation of a ternary mixture of organic compounds and
identification including derivative preparations using micro -scale
technique
1. Separation of a ternary mixture (S -S-S, S-S-L, S-L-L and L -L-L) (for
solid mixture: water insoluble/ soluble including carbohydrates) based
upon differences in the physical and the chemical properties of the
components.
2. Identification of the two components (indicated by the examiner) using
micro -scale technique.
3. Preparation of derivatives (any one of separated compound).
(Minimum 8 experiments )
Course code: PSCHO3P2
Single step organic preparation(1.0 g scale) involving purification by
Steam distillation / Vacuum distillation or Column chromatography.
1. Preparation of acetanilide from aniline and acetic acid using Zn dust.
(Purification by column chromatography)
2. Preparation of 1 -nitronaphthalene from naphthalene. (Purification by
steam distillation)
3. .Preparation of acetyl ferrocene from ferrocene. (Purification by column
chromatography)
4. .Preparation of 3 -nitroaniline from 1,3 -dinitrobenzene. (Purification b y
column chromatography)
5. Preparation of benzyl alcohol from benzaldehyde. (Purification by
vacuum distillation).
6. Preparation of methyl salicylate from salicylic acid. (Purification by
vacuum distillation).
7. .Preparation of 4 -methylacetophenone fro m toluene. (Purification by
vacuum distillation).
8. .Preparation of phenyl acetate from phenol. (Purification by vacuum
distillation)
9. Preparation of 2 -chlorotoluene from o-toluidine. (Purification by steam
distillation)
10. Preparation of 4 -nitrophenol from phenol. (Purification by steam
distillation/ column chromatography)
11. Preparation of fluorenone from fluorene . (Purification by column
chromatography)
12. Preparation of dimethylphthalate from phthalic anhydride. (Purification
by vacuum distillat ion)
(Minimum 8 experiments)
Note:
1. Students are expected to know (i) the planning of synthesis, effect of
reaction parameters including stoichiometry, and safety aspects including
MSDS (ii) the possible mechanism, expected spectral data (IR and NMR)
of the starting material and final product.
2. Students are expected to purify the product by Steam distillation /
Vacuum distillation or Column chromatography , measure its mass or
volume, c heck the purity by TLC, determine physical constant and
calculate percentage yield.
References for Practicals
1. Comprehensive Practical Organic Chemistry: Preparation and
Quantitative Analysis - V.K. Ahluwalia and Renu Aggarwal, Universities
Press India Ltd., 2000
2. Advanced Practical Organic Chemistry – N. K. Vishnoi, Third Addition,
Vikas Publishing House PVT Ltd
3. Systematic Laboratory Experiments in Organic Synthesis - A. Sethi, New
Age International Publications
4. Systematic Identification of Organic compounds, 6th edition, R. L.
Shriner, R. C. Fuson and D.Y. Curtin Wiley, New York.
5. Vogel's Textbook of Quantitative Analysis, revised, J. Bassett, R. C.
Denney, G. H. Jeffery and J. Mendham, ELBS
6. Experiments and Techniques in Organic Chemis try, D. Pasto, C. Johnson
and M. Miller, Prentice Hall
7. Macro -scale and Micro -scale Organic Experiments, K. L. Williamson, D.
C. Heath.
8. Systematic Qualitative Organic Analysis, H. Middleton, Adward Arnold.
9. Handbook of Organic Analysis - Qualitative and Quantitative, H. Clark,
Adward Arnold.
10. Vogel's Textbook of Practical Organic Chemistry, Fifth edition,2008,
B.S.Furniss, A. J.Hannaford, P. W. G. Smith, A. R. Tatchell, Pearson
Education.
11. Laboratory Manual of Organic Chemistry, Fifth edition, R K Bansal,
New Age Publishers.
12. Organic structures from spectra, L. D. Field, S. Sternhell, John R.
Kalman, Wiley, 4th ed., 2011.
1. The candidate is expected to submit a journal and project certified by the
Head of the Department /institution at the time of the practical examination.
2. A candidate will not be allowed to appear for the practical examination
unless he/she produces a certified journal or a certificate from the Head of
the institution/department stating that the journal is lost and the candidate
has performed the required number of experiments satisfactorily. The list of
the experiments performed by the candidate should be attached with such
certificate.
3. Use of non -programmable calculator is allowed both at the theory and the
practica l examination.
Semester – IV
Course Code: PSCH O401
Paper - I (Theoretical organic chemistry -II)
Unit 1 : Physical organic chemistry [15L]
1.1 Structural effects and reactivity : Linear free energy relationship (LFER) in
determination of organic reaction mechanism, The Hammett equation,
substituent constants, theories of substituent effects, interpretation of σ -
values, reaction constants ρ, Yukawa -Tsuno equation . [7L]
1.2 Uses of Hammett equation, deviations from Hammett equation. Dual
parameter correlations, Inductive substituent constants. The Taft model, σ I
and σ R scales, steric parameters Es and β. Solvent effects, Okamoto -Brown
equation, Swain -Scott equation, Edward and Ritchie correlations,
Grunwald -Winstein equation, Dimroth’s E T parameter, Solvatochromism Z -
scale , Spectroscopic Correlations, Thermodynamic Implications. [8L]
Unit 2 Supramolecular chemistry [15L]
2.1 Principles of molecular associations and organizations as exemplified in
biological macromolecules like nucleic acids, proteins and enzymes. [3L]
2.2 Synthetic molecular receptors: receptors with molecular cleft, molecular
tweezers, receptors with multiple hydrogen sites. [3L]
2.3 Structures and properties of crown ethers, cryptands, cyclophanes,
calixarenes, rotaxanes a nd cyclodextrins. Synthesis of crown ethers,
cryptands and calixarenes. [5L]
2.4 Molecular recognition and catalysis, molecular self -
assembly. Supramolecular Polymers, Gelsand Fibres . [4L]
Unit 3 Stereochemistry - II [15L]
3.1 Racemisation and resolution of racemates including conglomerates :
Mechanism of racemisation, methods of resolution: mechanical , chemical,
kinetic and equilibrium asymmetric transformation and through inclusion
compounds. [3L]
3.2 Determination of enantiomer and diastereomer composition: enzymatic
method, chromatographic methods. Methods based on NMR spectroscopy:
use of chiral derivatising agents (CDA), chiral solvating agents (CSA) and
Lanthanide shift reagents (LSR). [3L]
3.3 Correlative method for configurati onal assignment: chemical, optical
rotation, and NMR spectroscopy. [4L]
3.4 Molecular dissymmetry and chiroptical properties: Linearly and circularly
polarized light. Circular birefringence and circular dichroism. ORD and CD
curves. Cotton effect and its applications. The octant rule and the axial α –
haloketone rule with applications. [5L]
Unit 4 : Asymmetric synthesis [15L]
4.1 Principles of asymmetric synthesis: Introduction, the chiral pool in Nature,
methods of asymmetric induction – substrate, reagent and catalyst
controlled reactions. [3L]
4.2 Synthesis of L -DOPA [Knowles’s Mosanto process]. Asymmetric reactions
with mechanism: Aldol and related reactions, Cram’s rule, Felkin -Anh
model, Sharpless enantioselective epoxidation, hydroxylation,
aminohydroxylation, Diels -Alder reaction, reduction of prochiral carbonyl
compounds and olefins. [9L]
4.3 Use of chiral auxiliaries in diastereoselective reductions, asymmetric
amplification. Use of chiral BINOLs, BINAPs and chiral oxazolines
asymmetric transformations.
REFERENCES: [3L]
1 March’s Advanced Organic Chemistry, Jerry March, sixth edition,
2007, John Wiley and sons.
2 A guide to mechanism in Organic Chemistry, 6th edition, 2009,
Peter Sykes, Pearson education, New Delhi.
3 Advanced Organic Chemistry: Reaction Mechanisms, R. Bruckner,
Academic Press (2002).
4 Mechanism and theory in Organic Chemistry, T. H. Lowry and K.
C. Richardson, Harper and Row.
5 Organic Reaction Mechanism, 4th edition, V. K. Ahluvalia, R. K.
Parashar, Narosa Publication.
6 Reaction Mechanism in Organic Chemistry, S.M. Mukherji, S.P.
Singh, Macmillan Publishers, India.
7 Organic Chemistry, Part A and B, Fifth edition,2007, Francis A.
Carey and Richard J. Sundberg, Springer.
8 Carbenes, Nitrenes and Arynes. Von T. L. Gilchrist, C. W. Rees. Th.
Nelson and Sons Ltd., London 1969.
9 Organic reactive intermediates, Samuel P. MacManus, Academic
Press.
10 Organic Chemistry, J. Clayden, S. Warren, N. Greeves, P. Wothers,
1st Edition, Oxford University Press ( 2001).
11 Organic Chemistry, Seventh Edition, R.T. Morrison, R. N. Boyd &
S. K. Bhattacharjee, Pearson.Advanced Organic Chemistry: Reactions &
Mechanisms, second edition, B. Miller and R. Prasad, Pearson.
12 Organic reactions & their mechanisms, third revised edition, P.S.
Kalsi, New Age International Publishers.
13 Organic Chemistry: Structure and Function, P. Volhardt and N.
Schore, 5th Edition, 2012
14 Organic Chemistry, W. G. Solomons, C. B. Fryhle, , 9th Edition,
Wiley India Pvt. Ltd.,2009.
15 Pericyclic Reactions, S. San kararaman, Wiley VCH, 2005.
16 Advanced organic chemistry, Jagdamba Singh L. D. S. Yadav,
Pragati Prakashan, 2011
17 Pericyclic reactions, Ian Fleming, Oxford university press, 1999.
18 Pericyclic reactions -A mechanistic approach, S. M. Mukherji,
Macmillan Co. of India 1979.
19 Organic chemistry, 8th edition, John McMurry
20 Modern methods of Organic Synthesis, 4th Edition W. Carruthers
and Iain Coldham, Cambridge University Press 2004
21 Modern physical chemistry, Eric V Anslyn, Dennis A. Dougherty,
University science books,2006
22 Physical Organic Chemistry, N. S. Isaacs, ELBS/Longman
23 Stereochemistry of Carbon Compounds: Principles and
Applications, D, Nasipuri, 3rd edition, New Age International Ltd.
24 Stereochemistry of Organic Compounds, Ernest L. Eliel and Samuel
H. Wilen, Wiley -India edit
25 Stereochemistry, P. S. Kalsi, 4th edition, New Age International Ltd
26 Organic Stereochemistry, M. J. T. Robinson, Oxford University
Press, New Delhi, India edition, 2005
27 Bioorganic, Bioinorganic and Supramolecular chemistry, P.S. Kalsi
and J.P. Kalsi. New Age International Publishers
28 Supramolecular Chemistry; Concepts and Perspectives, J. M. Lehn,
VCH.
29 Crown ethers and analogous compounds, M. Hiraoka, Elsevier,
1992.
30 Large ring compounds, J.A.Semlyen, Wiley -VCH, 1997.
31 Fundamentals of Photochemistry, K. K. Rohtagi -Mukherji, Wiley -
Eastern
32 Essentials of Molecular Photochemistry, A. Gilbert and J. Baggott,
Blackwell Sciertific Publication.
33 Molecular Photochemistry, N. J. Turro, W. A. Benjamin.
34 Introductory Photochemistr y, A. Cox and T. Camp, McGraw -Hill
35 Photochemistry, R. P. Kundall and A. Gilbert, Thomson Nelson.
36 Organic Photochemistry, J. Coxon and B. Halton, Cambridge
University Press.
37 Molecular Orbitals and Organic Chemical Reactions by Ian Fleming
(Wiley – A john Wiley and Sons, Ltd., Publication)
Course Code: PSCHO402
Paper - II (Synthetic organic chemistry -II)
Unit 1: Designing Organic Synthesis -I [15L]
1.1 Protecting groups in Organic Synthesis: Protection and deprotection of
the hydroxyl, carbonyl, amino and carboxyl functional groups and its
applications. [3L]
1.2 Concept of umpolung (Reversal of polarity): Generation of acyl anion
equivalent using 1,3 -dithianes, methyl thiomethyl sulfoxides, cyanide ions,
cyanohydrin ethers, nitro compounds and vinylated ethers. [3L]
1.3 Introduction to Retrosynthetic analysis and synthetic planning: Linear
and convergent synthesis; Disconnection approach: An introduction to
synthons, synthetic equivalents, disconnection approach , functional group
interconversions (FGI), functional group addition (FGA), functional group
removal (FGR) importance of order of events in organic synthesis, one and
two group C -X disconnections (1,1; 1,2; 1,3 difunctionalized compounds),
selective organi c transformations: chemoselectivity, regiosel ectivity,
stereoselectivity, ena ntioselectivity . [9L]
Unit 2: Designing Organic Synthesis -II [15L]
2.1 General strategy: choosing a disconnection -simplification, symmetry, high
yielding steps, and recognisable starting material. [3L]
2.2 One group C -C Disconnections: Alcohols (including stereoslectivity),
carbonyls (including regioselectivity), Alkene synthesis, use of acetylenes
and aliphatic nitro compounds in organic synthesis. [6L]
2.3 Two group C -C Disconnections: 1,2- 1,3- 1,4- 1,5- and 1,6 -
difunctionalized compounds, Diels -Alder reactions, α, β -unsaturated
compounds, control in carbonyl condensations, Michael addition and
Robinson annelation. [6L]
Unit 3: Electro -organic chemistry and Selected methods of Organic synthesis [15L]
3.1 Electro -organic chemistry: [7L]
3.1.1 Introduction : Electrode potential, cell parameters, electrolyte, working
electrode, choice of solvents, supporting electrolytes .
3.1.2 Cathodic reduction: Reduction of alkyl halides, aldehydes, ketones, nitro
compounds, olefins, arenes, electro -dimerization .
3.1.3 Anodic oxidation: Oxidation of alkylbezene, Kolbe reaction, Non -Kolbe
oxidation, Shono oxidation .
3.2 Selected Methods of Organic synthesis [8L]
Applications of the following in organic synthesis:
3.2.1 Crown ethers, cryptands, micelles, cyclodextrins, catenanes .
3.2.2 Organocatalysts: Proline, Imidazolidinone .
3.2.3 Pd catalysed cycloaddition reactions : Stille reaction, Saeguse -Ito oxidation
to enones, Negishi coupling .
3.2.4 Use of Sc(OTf), and Yb(OTf) as water tolerant Lewis acid catalyst in aldol
condensation, Michael reaction, Diels -Alder reactio n, Friedel – Crafts
reaction.
Unit 4: Transition and rare earth metals in organic synthesis [15L]
4.1 Introduction to basic concepts: 18 electron rule, bonding in transition
metal complexes, C -H activation, oxidative addition, reductive elimina tion,
migratory insertion. [3L]
4.2 Palladium in organic synthe sis: π-bonding of Pd with olefins, applications
in C-C bond formation, carbonylation, alkene isomerisation, cross -coupling
of organometallics and halides. Representative examples: Heck reaction,
Suzuki -Miayura coupling, Sonogashira reaction and Wacker oxid ation.
Heteroatom coupling for bond formation between aryl/vinyl groups a nd N,
S, or P atoms. [5L]
4.3 Olefin metathesis using Grubb’s catalys t. [1L]
4.4 Application of Ni, Co, Fe, Rh, and Cr carbonyls in organic synthesis . [4L]
4.5 Application of samarium iodide including reduction of organic halides,
aldehydes and ketones, α -functionalised carbonyl and nitro compounds . [1L]
4.6 Application of Ce(IV) in synthesis of heterocyclic quinoxaline derivatives
and its role as a de -protecting agent .
REFERENCES: [1L]
Advanced Organic Chemistry, Part A and Part B: Reaction and
Synthesis, Francis A. Carey, Richard J. Sundberg, 5th Edition,
Springer Verlag
Modern Methods of Organic Synthesis, 4th Edition, W. Carruthers
and Iain Coldham, Cambridge University Press, 2004.
Chem.Rev. 2002, 102, 2227 -2302, Rare Earth Metal Triflates in
Organic Synthesis, S. Kobayashi, M. Sugiura, H. Kitagawa, and
W.W.L. Lam.
Organic Chemistry, Clayden Greeves Warren and Wothers,
Oxford Press (2001).
Moder Organic Synthe sis: An Introduction, G.S. Zweifel and
M.H. Nantz, W.H. Freeman and Company, (2007).
Advanced Organic Chemistry: Reaction Mechanism, R.
Bruckner, Academic Press (2002).
Principles of Organic Synthesis, R.O.C. Norman & J. M. Coxon,
3rd Edn., Nelson Thornes
Organic Chemistry, 7th Edn, R. T .Morrison, R. N. Boyd, & S. K.
Bhattacharjee, Pearson
Strategic Applications of Name Reactions in Organic Synthesis ,
L. Kurti & B. Czako (2005), Elsevier Academic Press
Advanced Organic Chemistry: Reactions & Mechanisms, 2nd
Edn., B. Miller & R. Prasad, Pearson
Organic reactions and their mechanisms, 3rd revisededition, P.S.
Kalsi, New Age International Publishers
Organic Synthesis: The Disconnection Approach, Stuart Warren,
John Wiley & Sons, 2004
Name Reactions and Reagen ts in Organic Synthesis, 2nd Edn.,
Bradford P. Mundy, Michael G. Ellard, and Frank Favoloro, Jr.,
Wiley -Interscience
Name Reactions, Jie Jack Lie, 3rd Edn., Springer
Organic Electrochemistry, H. Lund, and M. Baizer, 3rd Edn.,
Marcel Dekker.
Course Code: PSCHO403
Paper - III (Natural products and heterocyclic chemistry )
Unit 1 : Natural products -III [15L]
1.1 Steroids: General structure, classification. Occurrence, biological role,
important structural and stereochemical features of the following:
corticosteroids, steroidal hormones, steroidal alkaloids, sterols and bile
acids. [5L]
1.2 Synthesis of 16 -DPA from cholesterol and plant sapogenin. [2L]
1.3 Synthesis of the following from 16 -DPA: androste rone, testosterone,
oestrone, oestriol, oestradiol and progesterone. [5L]
1.4 Synthesis of cinerolone, jasmolone, allethrolone, exaltone and muscone. [3L]
Unit 2 : Natural products -IV [15L]
2.1 Vitamins: Classification, sources and biological importance of vitamin B 1,
B2, B6, folic acid, B 12, C, D 1, E (α -tocopherol), K 1, K2, H (β - biotin). [5L]
Synthesis of the following:
Vitamin A from β -ionone and bromoester moiety.
Vitamin B 1 including synthesis of pyrimidine and thiazole moieties
Vitamin B 2 from 3, 4 -dimethylaniline and D( -)ribose
Vitamin B 6 from: 1) ethoxyacetylacetone and cyanoacetamide, 2) ethyl
ester of N -formyl -DL-alanine (Harris synthesis)
Vitamin E (α -tocopherol) from trimethylquinol and phytyl bromide
Vitamin K 1 from 2 -methyl -1, 4-naphthaquinone and phytol.
2.2 Antibiotics: Classification on the basis of activity. Structure elucidation,
spectral data of penicillin -G, cephalosporin -C and chloramphenicol.
Synthesis of chloramphenicol (from benzaldehy de and β -nitroethanol)
penicillin -G and phenoxymethylpenicillin from D -penicillamine and t -butyl
phthalimide malonaldehyde (synthesis of D -penicillamine and t -butyl
phthalimide malonaldehyde expected). [6L]
2.3 Naturally occurring insecticides: Sources, structure and biological
properties of pyrethrums (pyrethrin I), rotenoids (rotenone). Synthesis of
pyrethrin I. [2L]
2.4 3.4 Terpenoids : Occurrence, classification, structure elucida tion, [2L]
stereochemistry, spectral data and synthesis of zingiberene .
Unit 3: Heterocyclic compounds -I [15L]
Heterocyclic compounds: Introduction, classification, Nomenclature of
heterocyclic compounds of monocyclic (3 -6 membered) (Common,
systematic (Hantzsch -Widman ) and replacement nomenclature)
Structure, reactivity, synthesis and reactions of pyrazole, imidazole,
oxazole, isoxazole, thiazole, isothiazole, pyridazi nes, pyrimidine, pyrazines
and oxazines .
Unit 4 : Heterocyclic compounds -II [15L]
Nomenclature of heterocyclic compounds of bicyclic/tricyclic (5 -6
Membered) fused heterocycles (up to three hetero atoms) . (Common,
systematic (Hantzsch -Widman ) and replacement nomenclature)
Nucleophilic ring opening reactions of oxiranes, aziridines, oxetanes and
azetidines.
Structure, reactivity, synthesis and reactions of coumarins, quinoxalines,
cinnolines, indole , benzimidazoles, benzoxazoles, benzothiazoles, Purines
and acridines .
REFERENCES:
1. Natural product chemistry, A mechanistic, biosynthetic and
ecological approach, Kurt B.G. Torssell, Apotekarsocieteten –
Swedish Pharmaceutical Press.
2. Natural products chemistry and applications, Sujata V. Bhat, B.A.
Nagasampagi and S. Meenakshi, Narosa Publishing House, 2011.
3. Organic Chemistry Natural Products Volume -II, O. P. Agarwal,
Krishna Prakashan, 2011.
4. Chemistry of natural products, F. F. Bentle y and F. R. Dollish, 1974
5. Natural Product Chemistry Vol.1 and 2, K. Nakanishi J. Goto. S.Ito
Majori and S. Nozoo, Academic Press, 1974.
6. Chemistry of natural products, V.K. Ahluwalia, Vishal Publishing
Co. 2008.
7. Heterocyclic chemistry, 3rd edition, Thomas L. Gilchrist, Pearson
Education, 2007.
8. Heterocyclic Chemistry, Synthesis, Reactions and Mechanisms , R.
K. Bansal, Wiley
Eastern Ltd., 1990.
9. Heterocyclic Chemistry , J. A. Joule and G. F. Smith , ELBS, 2nd
edition, 1982.
10. The Conformational Analysis of Heterocyclic Compounds , F.G.
Riddell, Academic Press,1980.
11. Principles of Modern Heterocyclic Chemistry , L.A. Paquette, W.B.
Benjamin, Inc., 1978.
12. An Introduction to the Chemistry of Heterocyclic Compounds , 2nd
edition, B.M. Acheson, 1975.
13. Natural Products: Chemistry and Biological Significance
Interscience, J. Mann, R.S.Davidson, J.B.Hobbs, D.V. Banthrope
and J. B. Harborne, Longman,Essex, 1994.
14. Organic Chemistry, Vol 2, I.L. Finar, ELBS, 6th edition, Pearson.
15. Stereoselective Synthesis: A Practical Approach, M. Nogradi,
Wiley -VCH, 1995.
16. Rodd’s Chemistry of Carbon Compounds, Ed. S. Coffey, Elsevier.
17. Chemistry, Biological and Pharmacological Properties of Medicinal
Plants from the Americas, Ed. Kurt Hostettmann, M.P. Gupta and A .
Marston, Harwood Academic Publishers.
18. Introduction to Flavonoids, B.A. Bohm, Harwood Academic
Publishers, 1998.
19. New Trends in Natural Product Chemistry, Atta -ur-Rahman and
M.I. Choudhary, Harwood Academic Publishers, 1998.
20. Insecticides of Natural Origin, Sukh Dev, Harwood Academic
Publishers.
21. Total. Synthesis of Longifolene, J. Am. Chem. Soc ., E. J. Corey, M.
Ohno, R. B. Mitra, and P. A. Vatakencherry. 1964, 86, 478.
22. Total. Synthesis of Longifolene, J. Am. Chem. Soc . 1961 , 83, 1251 .
23. The structure and total synthesis of 5 -Vetivone, J. A. Marshall
and P. C. Johnson, J. Org. Chem., 35, 192 (1970).
24. Total synthesis of spirovetivanes, J. Am. Chem. Soc. 1967, 89,
2750.
25. The Total Synthesis of Reserpine, Woodward, R. B.; Bader, F. E.;
Bickel, H., Frey, A. J.; K ierstead, R. W. Tetrahedron 1958 , 2, 1-57.
26. Total synthesis of Griseofulvin, Stork, G.; Tomasz, M. J. Am.
Chem. Soc. 1962, 84, 310.
27. Synthesis of (±) -4-demethoxydaunomycinone, A. V. Rama Rao ,
G. Venkatswamy , S. M. Javeed M. , V. H. Deshpande , B.
Ramamohan Rao , J. Org. Chem. , 1983, 48 (9), 1552.
28. The Alkaloids, The fundamental Chemistry A biogenetic approach,
Marcel Dekker Inc. New York, 1979.
29. Comprehensive Organic Chemistry by Barton and Olis, Pergamon
Press, Oxford, 1979.
30. Medicinal Natural Products, a Biosynthetic Approach, Derick Paul,
John Wiley and Sons, 2002.
31. Biosynthesis of Natural Products, Mannitto Paolo, Ellis Horwoocl
Limited, 1981.
32. Selected Organic synthesis, Ian Fleming, John Wiley and Sons,
1973.
33. Total synthesis of Natural Products, J. Apsimon, John Wiley
and Sons.
34. The Logic of Chemical Synthesis, E. J. Corey and Xue -Min Cheng,
Wiley Interscience.
35. Classics in Total Synthesis , K. C. Nicolaou and E. J. Sorensen,
Weinhem: VCH, 1996.
36. Spectroscopy of Organic compounds, P.S. Kalsi, New Age
International Pub. Ltd. And Wiley Eastern Ltd., Second edition,
1995.
37. Applications of Absorption Spectroscopy of Organic compounds, J.
R. Dyer, Prentice Hall of India, 1987.
38. Spectrometric Identification of Organic compounds, R.M.
Silverstein and others, John Wiley and Sons Inc., 5th ed., 1991
39. Absorption spectroscopy of organic Molecules, V.M. Parikh, 1974.
40. Spectroscopic methods in organi c chemistry, Williams and Fleming,
Tata McGraw Hill, 4th ed, 1989.
41. Organic spectroscopy, William Kemp, ELBS, 3rd ed., 1987.
42. Organic structures from spectra, L. D. Field , S. Sternhell , John R.
Kalman , Wiley, 4th ed., 3122.
43. Introduction to spectroscopy, Donald L. Pavia , Gary M. Lampman ,
George S. Kriz , James R. Vyvyan, 4th ed., 2 009.
44. Organic spectroscopic structure determination : a problem -based
learning approach Douglass F. Taber , Oxford University Press, 17-
Sep-2007 .
45. Organic Spectroscopy : Principles And Applications, Jag Mohan ,
Alpha Science International Ltd., 30-Mar-2004
46. Alkaloids,V.K. Ahuluwalia,Ane Books Pvt.Ltd.
47. Biotransformations in Organic Chemistry, 5thEdition, Kurt Faber,
Springer
48. Structure Determination of Organic Compounds, EPretsch, P.
Buhlmann, C.Affolter, Springer
Course Code: PSCHO OC-I 404
Paper – IV (INTELLECTUAL PROPERTY RIGHTS &
CHEMINFORMATICS )
Unit 1: [15L]
Introduction to Intellectual Property: [2L] [2L]
Historical Perspective, Different types of IP, Importance of protecting IP.
Patents: [5L] [5L]
Historical Perspective, Basic and associated right, WIPO, PCT system,
Traditional Knowledge, Patents and Health care -balancing promoting
innovation with public health, Software patents and their importance for
India.
Industrial Designs: [2L] [2L]
Definition, How to obtain, features, International design registration.
Copyrights: [2L] [2L]
Introduction, How to obtain, Differences from Patents.
Trade Marks: [2L] [2L]
Introduction, How to obtain, Different types of marks – Collective marks,
certification marks, service marks, trade names etc.
Geographical Indications: [2L] [2L]
Definition, rules for registration, prevention of illegal exploitation,
importance to India.
Unit 2: [15L] [15L]
Trade Secrets: [2L] [2L]
Introduction and Historical Perspectives, Scope of Protection, Risks
involved and legal aspects of Trade Secret Protection.
IP Infringement issue and enforcement: [2L] [2L]
Role of Judiciary, Role of law enforcement agencies – Police, Customs etc.
Economic Value of Intellectual Property: [5L] [2L]
Intangible assests and their valuation, Intellectual Property in the Indian
context – Various Laws in India Licensing and Technology transfer.
Different International agreements: [6L]
(a) World Trade Organization (WTO): [5L]
(i) General Agreement on Tariffs and Trade (GATT), Trade
Related Intellectual Property Rights (TRIPS) agreement
(ii) General Agreement on Trade Related Services (GATS)
Madrid Protocol.
(iii) Berne Convention
(iv) Budapest Treaty
(b) Paris Convention [6L]
WIPO and TRIPS, IPR and Plant Breeders Rights, IPR and Biodiversity.
Unit III: [15L] [15L]
Introduction to Cheminformatics: [5L] [5L]
History and evolution of cheminformatics, Use of Cheminformatics,
Prospects of cheminformatics, Molecular modeling and structure
elucidation.
Representation of molecules and chemical reactions: [5L] [5L]
Nomenclature, Different types of notations, SMILES coding, Matrix
representations, Structure of Molfiles and Sdfiles, Libraries and toolkits,
Different electronic effects, Reaction classification.
Searchi ng Chemical Structures: [5L] [5L]
Full structure search, sub -structure search, basic ideas, similarity search,
three dimensional search methods, basics of computation of physical and
chemical data and structure descriptors, data visualization.
Unit IV: [15L] [15L]
Applications:
Prediction of Properties of Compound, Linear Free Energy Relations,
Quantitative Structure – Property Relations, Descriptor Analysis, Model
Building, Modeling Toxicity, Structure – Spectra correlations, Prediction
NMR, IR and Mass spectra, Computer Assisted Struc ture elucidations,
Computer assi sted Synthesis Design, Introduction to drug design, Target
Identification and Validation, Lead Finding and Optimization, analysis of
HTS data, Virtual Screening, Design of Com binatorial Libraries, Ligand -
based and Structure based Drug design, Application of Cheminformatics in
Drug Design.
REFERENCES:
1. Andrew R. Leach & Valerie J. Gillet (2007) An Introduction to
Cheminformatics. Springer: The Netherlands.
2. Gasteiger, J. & Engel, T. (2003) Cheminformatics: A textbook .
Wiley –VCH
3. Gupta, S. P. QSAR and Molecular Modeling. Springer -Anamaya
Pub.: New Delhi.
Course Code: PSCHO OC-II 404
PAPER – IV: RESEARCH METHODOLOGY
Unit 1: [15L] [15L]
Print: [5L] [5L]
Primary, Secondary and Tertiary sources.
Journals:
Journal abbreviations, abstracts, current titles, reviews, monographs,
dictionaries, text -books, current contents, Introduction to Chemical
Abstracts and Beilstein, Subject Index, Substance Index, Author Index,
Formula Index, and other Indices with examples.
Digital: [5L] [5L]
Web sources, E -journals, Journal access, TOC alerts, Hot articles, Citation
Index, Impact factor, H -index, E -consortium, UGC infonet, E -books,
Internet discussion groups and communities, Blogs, preprint servers, Search
engines, Scirus, Google Scholar, ChemIndustry, Wiki -databases,
ChemSpider, Science Direct, SciFinder, Scopus.
Information Technology and Library Resources: [5L] [5L]
The Internet and World wide web, Internet resources for Chemistry, finding
and citing published information.
Unit II: DATA ANALYSIS [15L] [15L]
The Investigative Approach:
Making and recording Measurements, SI units and their use, Scientific
methods and design of experiments.
Analysis and Presentation of Data:
Descriptive statistics, choosing and using statistical tests, Chemometrics ,
Analysis of Variance (ANOVA), Correlation and regression, curve fitting,
fitting of linear equations, simple linear cases, weighted linear case, analysis
of residuals, general polynomial fitting, linearizing transformations,
exponential function fit, r a nd its abuse, basic aspects of multiple linear
regression analysis.
Unit III: METHODS OF SCIENTIFIC RESEARCH AND WRITING [15L]
SCIENTIFIC PAPERS [15L]
Reporting practical and project work, Writing literature surveys and
reviews, organizing a poster display, giving an oral presentation.
Writing Scientific Papers:
Justification for scientific contributions, bibliography, description of
methods, conclusions, the need for illustration, style, publications of
scientific work, writing ethics, avoiding plagiarism.
Unit IV: CHEMICAL SAFETY & ETHICAL HANDLING OF
CHEMICALS [15L] [15L]
Safe working procedure and protective environment, protective apparel,
emergency procedure, first aid, laboratory ventilation, safe storage and use
of hazardous chemicals, procedure for working with substances that pose
hazards, fla mmable or explosive hazards, procedures for working with
gases at pressures above or below atmospheric pressur, safe storage and
disposal of waste chemicals, recovery, recycling and reuse of laboratory
chemicals, procedure for laboratory disposal of explos ives, identification,
verification and segregation of laboratory waste, disposal of chemicals in
the sanitary sewer system, incineration and transportation of hazardous
chemicals.
REFERENCES:
1. Dean, J. R., Jones, A. M., Holmes, D., Reed, R., Weyers, J., &
Jones, A., (2011), Practical skills in Chemistry, 2nd Ed., Prentice
Hall, Harlow.
2. Hibbert, D. B. & Gooding, J. J. (2006) Data Analysis for Chemistry
Oxford University Press.
3. Topping, J., (1984 ) Errors of Observation and their Treatment 4th
Ed., Chapman Hill, London.
4. Harris, D. C. (2007) Quantative Chemical Analysis 6th Ed., Freeman
Chapters 3 -5
5. Levie, R. De. (2001) How to use Excel in Analytical Chemistryand
in general scientific data analysis Cambridge Universty Press.
6. Chemical Safety matters – IUPAC -IPCS, (1992) Cambridge
University Press.
7. OSU Safety manual 1.01
Semester IV: Practicals
Course code: PSCHO4P1
Two steps preparations
1. Acetophenone → Acetophenone phenyl hydrazine → 2 -phenyl
indole.
2. 2-naphthol → 1 -phenyl azo -2-naphthol → 1 -amino -2-naphthol.
3. Cyclohexanone → cyclohexanone oxime → Caprolactum.
4. Hydroquinone → hydroquinone diacetate → 2,5-
dihydroxyacetophenone .
5. 4-nitrotoluene → 4-nitrobenzoic acid → 4 -aminobenzoic acid.
6. o-nitroaniline → o-phenylene diamine → Benzimidazole.
7. Benzophenone → benzophenone oxime → benz anilide .
8. o-chlorobenzoic acid → N -phenyl anthranilic acid → acridone.
9. Benzoin → benzil → benzilic acid.
10. Phthalic acid → phthalimide → anthranilic acid.
11. Resorcinol → 4-methyl -7-hydroxy coumarin → 4-methyl -7-acetoxy
coumarin.
12. Anthracene → anthraquinone → anthrone.
(Minimum 8 experiments)
Note:
1. Students are expected to know (i) the planning of synthesis, effect of
reaction parameters including stoichiometry, and safety aspects including
MSDS (ii) the possible mechanism, expected spectral data (IR and NMR)
of the starting material and final product.
2. Students are expected to purify the product by recryllization , measure its
mass or volume, check the purity by TLC, determine physical constant
and calculate percentage yield.
Course code: PSCHO4P 2
Session -I: Combined spectral identification: Interpretation of spectral
data of organic compounds (UV, IR, PMR, CMR and Mass spectra).
A student will be given UV, IR, PMR, CMR, and Mass spectra of a
compound from which preliminary information should be reported within
first half an hour of the examination without referring to any book/reference
material. The complete structure of the compound may then be
elucidated by referring to any standard text -book/reference material etc
(Minimum 8 spectral analysis).
Session -II: Project eva luation
References for Practicals
1. Comprehensive Practical Organic Chemistry: Preparation and
Quantitative Analysis - V.
K. Ahluwalia and Renu Aggarwal, Universities Press India Ltd., 2000
2. Advanced Practical Organic Chemistry – N. K. Vishnoi , Third Addition,
Vikas Publishing House PVT Ltd
3. Systematic Laboratory Experiments in Organic Synthesis - A. Sethi, New
Age International Publications
4. Systematic Identification of Organic compounds, 6th edition, R. L.
Shriner, R. C. Fuson and D.Y. Cur tin Wiley, New York.
5. Vogel's Textbook of Quantitative Analysis, revised, J. Bassett, R. C.
Denney, G. H. Jeffery and J. Mendham, ELBS
6. Experiments and Techniques in Organic Chemistry, D. Pasto, C. Johnson
and M. Miller, Prentice Hall
7. Macro -scale an d Micro -scale Organic Experiments, K. L. Williamson, D.
C. Heath.
8. Systematic Qualitative Organic Analysis, H. Middleton, Adward Arnold.
9. Handbook of Organic Analysis - Qualitative and Quantitative, H. Clark,
Adward Arnold.
10. Vogel's Textbook of Practical Organic Chemistry, Fifth edition,2008,
B.S.Furniss, A. J.Hannaford, P. W. G. Smith, A. R. Tatchell, Pearson
Education.
11. Laboratory Manual of Organic Chemistry, Fifth edition, R K Bansal,
New Age Publishers.
12. Organic structures from spectra, L. D. Field, S. Sternhell, John R.
Kalman, Wiley, 4th ed., 2011.
1. The candidate is expected to submit a journal and project certified by the
Head of the Department /institution at the time of the practical examination.
2. A ca ndidate will not be allowed to appear for the practical examination
unless he/she produces a certified journal or a certificate from the Head of
the institution/department stating that the journal is lost and the candidate
has performed the required number of experiments satisfactorily. The list of
the experiments performed by the candidate should be attached with such
certificate.
3. Use of non -programmable calculator is allowed both at the theory and the
practical examination.