Mangalore University

Department of Studies in Chemistry

M. Sc. Degree Programme
(CHOICE BASED CREDIT SYSTEM - SEMESTER SCHEME)

Syllabi for M.Sc., Courses in

ORGANIC CHEMISTRY
(From the Academic Year 2016-17 onwards)
 Programme : M.Sc. in ORGANIC CHEMISTRY

1st Semester 2nd Semester

Course Course Title Course Course Title

Code Code
OC H 401 Inorganic Chemistry OC H 451 Advanced Inorganic Chemistry
OC H 402 Organic Chemistry OC H 452 Advanced Organic Chemistry
OC H 403 Physical Chemistry OC 453H Advanced Physical Chemistry
OH S 404 Inorganic Spectroscopy and OC S 454 Organic Spectroscopic
Analytical Techniques Or Techniques
OC S 405 Or OC 455 Or
Environmental Chemistry Chemistry of Bio-molecules
OC E 406 Molecular Spectroscoy and OC E 456 Environmental, Electro- and
Diffraction Techniques Polymer Chemistry
OC P 407 Inorganic Chemistry OC P 457 Inorganic Chemistry Practicals-
Practicals-I II
OC P 408 Organic Chemistry Practicals-I OC P 458 Organic Chemistry Practicals-II
OC P Physical Chemistry Practicals- OC P 459 Physical Chemistry Practicals-II
409S I

3rd Semester 4th Semester

OC H 501 Organic Reaction Mechanism OC H 551 Organic Synthetic Methods

OC H 502 Synthetic Reagents and OC H 552 Medicinal Chemistry
Spectroscopic Techniques
OC H 503 Advanced Heterocyclic OC H 553 Natural Products Chemistry
Chemistry
OC S 504 Organic Photochemistry & OC S 554 Synthetic Polymers, Dyes &
Or Pericyclic Reactions Pesticides
OC S 505 Or
Bioorganic Chemistry
OC E 506 Analytical and Green Chemistry OC S 555 Separation Techniques and
Or Organometallic Chemistry
OC S 556 Or
Organic Synthetic Strategies
and Petrochemicals
OC P 507 Organic Chemistry Practicals-III OC H 557 Organic Chemistry Practicals-
VI
OC P 508 Organic Chemistry Practicals-IV OC H 558 Organic Chemistry Practicals-
VII
OC P 509 Organic Chemistry Practicals-V OC H 559 Project Work & Dissertation
 3rd SEMESTER

OC H 501: Organic Reaction Mechanism

UNIT I: [15 Hours]

Organic Name Reactions: Reactions, Mechanisms and synthetic uses of the following:
Stobbe condensation, Darzen condensation, Gattermann-Koch reaction, Cannizzaro
reaction,Duff reaction Chichibabin reaction, Benzoin condensation, Claisen-Schmidt
condensation, Claisen reaction, Simon-Smith reaction, Stork Enamine reactions, Sharpless
asymmetric epoxidation, Hofmann-Loffler-Freytag reaction, Suzuki coupling, Heck reaction,
Woodward and Prevost Hydroxylation, Bucherer reaction, Ullmann reaction. Wittig reaction-
Mitsunobu reaction, Stephen reaction.

UNIT- II: [15 Hours]

Molecular Rearrangements: Classification and general mechanistic treatment of
nucleophilic, electrophilic and free radical rearrangements. Intermolecular and Intramolecular
migration, nature of migration and migratory aptitudes. Mechanism of Wagner-Meerwein,
Dienone-Phenol, Pinacol-Pinacolone, Demyanov, Benzil-Benzilic acid, Fries, Wolff,
Favorskii, Neber, Benzidine, Baeyer-Villiger, Beckmann, Lossen, Curtius, Schmidt, Stevens,
Shapiro, Baker-Venkatraman and Amadori rearrangement.

UNIT- III: [15 Hours]

Synthetic Design: Carbon skeleton frame work, Classification of carbon-carbon single bond
and double bond forming reaction and their use in carbon skeleton ring formation. Ring
forming and ring cleaving reactions, use of Thorpe condensation, Carbene insertion reaction,
Friedel-Crafts reaction, 1,3-dipolar addition and Ene reaction in ring formation, Oxidative
cleavage of rings and Retro Diel’s-Alder reactions.
Planning of Organic Synthesis: Selection of starting materials and key intermediates during
the synthesis. Synthesis of Cubane and Iswarane. Use of Robinson annulation, Dieckmann
cyclisation, Arndt-Eistert synthesis, Diel’s- Alder reaction in organic synthesis.
Functionality: Synthesis of 6- and 7- methoxy tetralones, biotin and penicillin-V with
special reference to the introduction of functional groups. Stereo chemical consideration and
stereo selectivity during organic synthesis.

References:
1. Advanced Organic Chemistry- Part A & B-Francis A Carey and R. J. Sundberg (Plenum)
3. Organic Chemistry, Vol 1-3 Mukherji Singh and Kapoor (Wiley Eastern, New Delhi)
4. Synthetic Organic Chemistry- G.R.Chatwal (Himalaya, Bombay), 1994.
5. Organic Reaction Mechanisms-V.K.Ahluw alia & R.K.Parashar (Narovasa publishing house), 2006
6. Organic Chemistry, Vol I-II, I.L.Finar (Longmann ELBS, London), 1973.
7. Advanced Organic Chemistry:Reaction Mechanisms- Reinhard Bruckner (Academic), 2005.
8. Organic Reactions and their mechanisms-P.S.Kalsi (New Age, New Delhi), 1996.
9. Organic Synthesis- R. E. Ireland (Prentice Hall India), 1969.
10. Art in Organic Synthesis- Anand, Bindra & Ranganath-(Wiley New Delhi), 1970.
11. Modern Methods of Organic Synthesis-N.Carruthers (Cambridge University), 1996.
 OC H 502: Synthetic Reagents and Spectroscopic Techniques
UNIT- I: Reagents in Organic Synthesis-I [15 Hours]
Organometallic Reagents: Preparation and properties of Organolithium and
organomagnesium compounds. Their uses in organic synthesis and in the preparation of
Organometallic compounds.
Methods of preparation, properties, reactivity and reactions of Organozinc, Organocadmium,
Organomercury Organoindium, Organoaluminium and Organotellurium reagents.
Silicon containing Reagents: Introduction, preparation reactions & stereochemistry, Peterson
reaction.
Boron containing Reagents: Introduction, preparations, Hydroborations, reactions of
Organoboranes- Isomerization, oxidation, protonolysis, carbonylation, cyanidation. Synthesis
of esters, E and Z alkenes, conjugated dienes and alkynes.
Organotin Compounds: Synthesis of Organostannanes and their utility in C-C bond forming
reactions. Tributyltin hydride, Barton decarboxylation reaction, Barton deoxygenation,
Stelly-Kelly coupling reaction.

UNIT- II: Reagents in Organic Synthesis-II [15 Hours]

Use of the following reagents in Organic synthesis and functional group transformation:
Gillman’s reagent, Lithium diisopropylamide (LDA), Dicyclohexyl carbodiimide (DCC), 1,3-
dithiane (reactivity-umpolong), Trimethyl silyliodide, DDQ, Selenium dioxide, Wilkinsons
catalyst, Phase transfer catalysts, Baker’s yeast, Polyphosphoric acid. Trimethyl silyl
cyanide, Hydrosilanes, Chloramine-T, Aluminium iso-propoxide. Woodward and Prevost
hydroxylation, Zeigler-Natta catalyst, Phase transfer catalysts, Crown ethers.

UNIT –III: [15 Hours]

IR,1H NMR and 13C-NMR: Characteristic vibrational frequencies of alkanes, alkenes,
alkynes, aromatic compounds, alcohols, ethers, phenols and amines. Detailed study of
vibrational frequencies of carbonyl compounds (Ketones, aldehydes, esters, amides, acids,
anhydrides, lactones, lactams and conjugated carbonyl compounds). Effect of H-bonding &
solvent effect on vibrational frequencies.
Chemical shift of different class of organic compounds. Spin-spin coupling – illustrate with
different examples. AB, AX-Spin system. Chemical exchange, effct of deuteration, complex
spin-spin interaction between two, three, four and five nuclei. Stereochemistry, hindered
rotation;Karplus-Curve. Variation of coupling constant with dihedral angle.Pulse
techniques,Techniques for simplication of spectra, Heteronuclear coupling,INDOR,2D-
NMR,FT-NMR.Applications of NMR
Composite problems involving the application of UV, IR,1H NMR and 13C-NMR and Mass
spectroscopy technique in the structural elucidation of organic molecules.
Green Techniques:
Crown Ethers: Introduction, Nomenclature, Synthesis of Dibenzo[18]crown-6, Aza-crown,
Cryptates, Synthetic applications like esterification, saponification, elimation reactions,
superoxide anion, generation of carbenes.
Microwave induced reactions: Introduction, advantages, limitations, precautions,
application like Deprotection, Hydrolysis, Condensation, ortho ester claisen rearrangement.
Ionic Liquids: Introduction, properties, types, preparation, applications like Epoxidation,
Alkene Metathesis, Oxidation, Reduction and Enzyme catalysed synthesis.
References :
1. Advanced Organic chemistry 5th edition -J. March (John Wiley and sons).
2. Organic Chemistry- J. Clayden, N. Greeves, S. Warren and P. Wothers (Oxford University
Press).
3. E. Eliel and S.H. Wilen, Stereochemistry of Organic compounds, John Wiley.
4. Organic Spectroscopy- William Kemp(Palgrave)2005.
5. Advanced Organic Chemistry – Part A & B, 3rd edition- F.A. Carey and Sundberg,
(Plenum Press) 1990.
6. Advanced General Organic Chemistry-S.K. Ghosh (Book and Alleied (P) Ltd) 1998.
7. Organic Synthesis, special Techniques -V.K. Ahluwalia and Renu Agrawal (Narosa
Publications).
8. Spectrometric Identification of Organic Compounds - Silverstein, Bassler & Monnill (Wiley)1981.
9. Spectroscopy of Organic Compounds-3rd Ed.-P.S.Kalsi (New Age, New Delhi) 2000.
10. Spectroscopic Methods in Organic Chemistry - Williams and Fleming, TMH.
11. Spectroscopy, Donald L.Pavia (Cengage learning India Pvt.Ltd., Delhi), 2007.
12. Organic Spectroscopy-3rd ed.-W.Kemp (Pagrave Publishers, New York), 1991.

OC H 503: Advanced Heterocyclic Chemistry

UNIT -II: Heterocyclic Chemistry-I [15 Hours]
Introduction, Biologically important heterocycles, Nomenclature of Heterocycles,
Replacement and systematic nomenclature, Hantzsch-Widman system for monocyclic, fused
and bridged heterocycles. Synthesis and reactions of three membered heterocycles-aziridines,
oxiranes, episulfides, diaziridines, oxazirines and diazirines. Synthesis and reactions of four
membered heterocycles-oxetanes, azetidines and thietanes. Synthesis & reactions of five
membered eterocycles-furan, pyrrole, thiophene, oxazoles, imidazoles and thiazoles.

UNIT -II: Heterocyclic Chemistry-II [15 Hours]

Structure, synthesis and reactions of six membered heterocycles- pyridine, α- and γ-Pyrones,
oxazines. Pyrazines, Pyridazines, Pyrimidines. Synthesis and reactions of seven
heterocycles-Azepines, Oxepines and Thiepines. Synthesis and reactions of fused
heterocycles- benzofuran, benzothiophene & indole.selenophenes, tellurophenes, Quinolines,
Isoquinolines, Coumarins, Naphthyridines and Purines.

UNIT -III: Heterocyclic Chemistry-III [15 Hours]

Mesoionic compounds: Introduction, Synthesis and reactions of sydnones.
Anthocyanins and Anthocyanidins: Introduction and general methods of synthesis.
Flavones, Flavonols and Isoflavones: Introduction and synthesis of flavone, flavonal and
quercetin. Structural elucidation and synthesis of Uric acid, Caffeine.
Heterocycles in functional group and ring transformations: Alkanes from thiophenes,
dienes from pyrroles, alcohols from isooxazolines, conversion of coumarin to benzofuran,
sydnone to pyrazole, chromones to pyrazoles, furans to pyridines, pyrrole to pyridines,
pyrimidine to pyrazole, isatins to quinolines, indoles to quinoline. Dimroth and Cornforth
rearrangements.

References:
1 An Introduction To the Chemistry of Heterocyclic Compounds-Acheson (Wiley Eastern),1997.
2. Heterocyclic Chemistry- J.Joule & G.Smith (Van Nostrand ELBS), 1978.
3. Polymer Science- V.R.Gowariker, N.V.Vishwanathan & T.Shridhar (Wiley Eastern)
4. Comprehensive Heterocyclic Chemistry Vol-I-VI Ed. Katritzky & Rees (Pergamon), 1984.
5. Organic Chemistry, Vol I & II, I.L.Finar (Longmann ELBS, London), 1973.
6. Natural Products Chemistry, Vol-I & II- G.R.Chatwal(Himalaya), 1990.
 OC S 504: Organic Photochemistry & Pericyclic Reactions
UNIT-I: Organic Photochemistry [12 Hours]
Bonding and antibonding orbital, σ and π orbitals, σ* and π* orbitals, singlet and triplet
states, relative energies and excited states, Chemistry of excited states of organic molecules,
Jablonski diagram and quantum yield, Photodissociation, Photoreduction, Photochemical
isomerisation, Photocyclisation and related reactions. Norrish Type-I and Type-II reactions,
Di-pi methane rearrangement, Optical pumping, Barton reaction and Photo Fries
rearrangement, Paterno-Buchi reaction, Photochemistry of alkenes, benzenes, Yang
cyclisation. Photochemistry of vision. photodegradation of polymers. Introduction to
Photochemical cells, energy conversion and storage. Photocatalysis: Photocleavage of waste
which are environmentally hazardous by using TiO2, Photooxidation and photoreduction
reactions.
UNIT-II: [12 Hours]
Photochemistry of Heterocycles: Photo-oxidation of pyrroles, photochemical reactions of
pyrazoles, 1,2,3 and 1,2,4-triazoles, 1,2,3-triazines, 1,3,4-oxadiazoles, mono and disubstituted
tetrazoles. Photochemistry of pyridazines and pyrimidines. Photochemistry of five membered
heterocycles-with one heteroatom-Pyrrole, Furan and Thiophene; with two hetero atoms-
Thiazole, Oxazole, isoxazole and Pyrazole. Photochemistry of six and seven membered
heterocycles-Pyridine, Pyrones, Pyridazine and Pyrazine. Fused heterocycles-
Benzothiophene. Synthesis of Pyrazine from azirine derivatives. Photochemical reactions of
Pyrazine.
UNIT-III: [12 Hours]
Pericyclic Reactions: Introduction, Characteristics and classification of pericyclic reactions-
Electrocyclic, cycloaddition & cycloreversions and sigmatropic reactions. Aromatic Transition
States (ATS)/Perturbation Molecular Orbitals (PMO) approach for the interpretation of
mechanism of pericyclic reactions. Molecular orbital symmetry, Frontier orbitals of ethylene,
1,3-butadiene, 1,3,5-hexatriene and allyl systems. Woodward-Hoffmann correlation diagram
and FMO approach.
Electrocyclic Reactions: Introduction, Con-rotatory and dis-rotatory Process, 4n and 4n+2
systems. Reactions of cations and anions, formation and cyclisation of dipolar molecules.
Cycloaddition reaction: Suprafacial and Antrafacial addition, notation of cycloadditions,
2+2 and 4+2 systems, 2+2 additions of ketones, secondary effects of substitutes on the rates
of cycioadditions and chelotropic reactions. 1,3-dipolar cycloaddition reactions and their
applications in the synthesis of five membered heterocycles, nitrile oxid and sydnones.
Sigmatropic reactions: FMO approach and perturbation of molecular (PMO) approach for
the explanation of sigmatropic rearrgements under thermal and photochemical conditions.
Suprafacial and Antrafacial shift of H, [1,3] [1,5] [1,7] and [3,3]-sigmatropic shifts. Walk,
Claisen, Cope, Oxy-Cope and Aza-Cope rearrangements.

References:
1. Organic Photochemistry- Vol I & II- O.L. Chapman (Marcel Decker).
2. Organic Chemistry- Vol 1-3 - Mukherji Singh and Kapoor (Wiley Eastern).
3. Organic Reaction Mechanisms-V.K.Ahluwalia & R.K.Parashar (Narosa) 2006.
4. Advanced Organic Chemistry-Reaction Mechanisms, Reinhard Bruckner (Academic),
2005.
5. Pericyclic reactions, S.M Mukherji (McMillan) 1979.
6. J. A. Joule and G. F. Smith: Heterocyclic Chemistry, Cambidge University press (1972).
7. A. R. Katritzky and C. J. Rees: Comprehensive Heterocyclic Chemistry, Pergamon (1984).
8. D. H.R. Barton and W. D. Ollis: Comprehensive Organic Chemistry, Vol 14, Heterocyclic
Compounds, Pergamon (1979).
9. A. R. Katritzky: Advances in Heterocyclic Chemistry, Vol 15-25, Academic (1971-81).

OC S 505 : Bioorganic Chemistry

UNIT I [12 Hours]

Carbohydrates Configuration and conformation of monosaccharides, Hudsons rule,
Mutarotation. Chemistry of important derivatives of monosaccharides-ethers, esters, acetals,
ketals, deoxysugars, aminosugars, Structure of disaccharides-maltose, cellobiose and sucrose.
General methods of structural degradation of polysaccharides- methylation & partial
hydrolysis, Smith degradation and alkaline degradation techniques. Structures of cellulose,
chitin, starch and glycogen.

UNIT II [12 Hours]

Peptides & Proteins: Peptide bond formation and synthesis of polypeptides, Amino and
carboxy protecting groups in peptide synthesis, Solid phase peptide synthesis-Merrifield
method, Peptide structure determination-Sequence and End group anaysis (N-Terminus and
C-Terminus), Secondary, Tertiary and Quaternary structure of proteins.
Nucleic acids: Nucleosides and Nucleotides, Chemical synthesis of nucleosides and
nucleotides. Poly nucleotides- Structure and functions of DNA and RNA.
Non steroidal hormones: Study of the Oxytocin, Vasopressin and synthetic analogs, General
study of ACTH, Growth hormones, Somotropin and Insulin.

UNIT III [12 Hours]

Vitamins: Classification and Nomenclature. Source, deficiency diseases and biological
functions of Vitamins. Study of Vitamin A1, Vitamin B3, Vitamin B5, Vitamin C and Vitamin
K1.
Antibiotics: Introduction, Classification, Chemistry of Pencillin V, Streptomycin,
Chloramphenicol and Tetracyclin.

References:
1.Organic Chemistry-P.Y.Bruice (Pearson Education Pvt. Ltd.,New Delhi),2002.
2.Organic Chemistry 4th Edn.–S.H. Pine et al (McGraw-Hill, London) 1987.
3.Advanced Organic Chemistry- R.A. Carey and R.J. Sundberg (Plenum, New York)1990.
4. Organic Chemistry, Vol I & II, I.L.Finar (Longmann ELBS, London), 1973.
5. Natural Products Chemistry, Vol-I & II- G.R.Chatwal(Himalaya), 1990.

CH E 506 : ANALYTICAL AND GREEN CHEMISTYRY

UNIT- I: [12 Hours]

UV/Electronic Spectroscopy: Basic principles, Beer-Lambert law, types of absorption
bands, Factors affecting the positions of UV bands. Theoretical prediction of max for
polyenes, ,-unsaturated aldehydes, ketones (Woodward-Fieser rules) and substituted
benzenes.
IR Spectroscopy: Basic principles, Application of infrared spectroscopy in the structural
study-identity by finger printing and identification of functional groups. Characteristic
vibrational frequencies of alkanes, alkenes, alkynes, aromatic compounds, alcohols, ethers,
phenols and amines). Study of vibrational frequencies of carbonyl compounds (ketones,
aldehydes, esters, amides and acids). Factors affecting band positions and intensities
Nuclear Magnetic Resonance Spectroscopy: Basic principles, Solvents used, chemical shift
and its measurements, factors affecting chemical shift. Integration of NMR signals, spin-spin
coupling, coupling constant. Shielding and deshielding. High resolution 1H NMR.
Applications of NMR spectroscopy in structure elucidation of simple organic molecules.
Mass Spectrometry: Basic principles, molecular ions, meta-stable ions and isotope ions.
Fragmentation processes, McLafferty rearrangement. retro Diels-Alder fragmentations.
Nitrogen rule.

UNIT- II: [12 Hours]

Hydrologic cycle, sources, chemistry of sea water, criteria and standards of water quality-
safe drinking water, maximum contamination levels of inorganic and organic chemicals,
radiological contaminants, turbidity, microbial contaminants. Public health significance and
measurement of colour, turbidity, total solids, acidity, alkalinity, hardness, chloride, residual
chlorine, sulphate, fluoride, phosphate and different forms of nitrogen in natural and polluted
water. Chemical sources of taste and odour, treatment for their removal, sampling and
monitoring techniques. Determination and significance of DO, BOD ,COD and TOC. Water
purification for drinking and industrial purposes, disinfection techniques, demineralization,
desalination processes and reverse osmosis . Treatment of liquid radioactive wastes

UNIT- III: [12 Hours]

Green Chemistry: Definition and principles, planning a green synthesis in a chemical
laboratory, Green preparation-Aqueous phase reactions, solid state (solventless) reactions,
photochemical reactions, Phase transfer catalyst catalysed reactions (Quaternary ammonium
salts & Crown ethers), enzymatic transformations & reactions in ionic liquids.
Sonochemistry: Introduction, instrumentation, the phenomenon of cavitation, Sonochemical
esterification, substitution, addition, oxidation, reduction and coupling reactions.
Microwave induced organic synthesis: Introduction, reaction vessel and reaction medium,
concept, specific effect, atom efficiency, % atom utilisation, advantages and limitations,
alkylation of active methylene compounds, N-alkylation, condensation of active methylene
compounds with aldehydes, Diels-Alder reaction, Leuckardt reductive amination of ketones,
ortho ester Claisen rearrangement.

References:
1. Organic Spectroscopy-3rd Ed.-W.Kemp (Pagrave Publishers, New York), 1991.
2. Spectrometric Identification of Organic Compounds - Silverstein, Bassler & Monnill
(Wiley)1981.
3. Applications of Absorption Spectroscopy of Organic Compounds-Dyer(Prentice Hall,NY)
1965.
4. Spectroscopy of Organic Compounds-3rd Ed.-P.S.Kalsi (New Age, New Delhi) 2000.
5. Spectroscopic Methods in Organic Chemistry - Williams and Fleming, TMH.
6. A.K. De : Environmental Chemistry, (Wiley Eastern).
7. S.K.Banerji : Environmental Chemistry, ( Prentice Hall India), 1993.
8 S.D. Faust and O.M. Aly : Chemistry of Water Treatment, (Butterworths),1983.
9. Sawyer and McCarty, Chemistry for Environmental Engineering(McGraw Hill) 1978
10. I.Williams, Environmental Chemistry, John Wiley, 2001.
11. S.M.Khopkar, Environmental Pollution Analysis, (Wiley Eastern).
12. Organic Synthesis-Special Techniques, V.K.Ahluwalia & R. Aggarwal, Narosa, 2001.
13. Green Chemistry-Environment friendly alternatives- R.Sanghi & M.M.Srivatsava,
Narosa, 2003.
14. Green Chemistry-Environment benign reactions- V.K.Ahluwalia, Ane Books India, 2006.

OC P 507: Organic Chemistry Practicals – III

Quantitative determination of sugars, amino acids, phenols, carboxylic acids, amides, esters,
aldehydes, ketones, urea by various methods. Determinations of acid & ester and acid &
amide in the mixtures.
Determination of functional groups like hydroxyl, vic-hydroxyl, enol, amino, amide,
unsaturation and nitro groups by various methods. Semi-micro analysis of Nitrogen, Halogen,
Alkoxy, C-methyl and active hydrogens.

OC P 508: Organic Chemistry Practicals – IV

Isolation and Charecterization of natural products like Caffeine, Recinoleic acid, Azelic acid,
Piperine, Hespiridine, Cysteine, Casein, Lycopene and enzymes like Lipase and Sucrase.
Extraction of Groundnut oil and Coconut oil. Determination of Saponification oils and fats,
Determination of Iodine values of oils and fats using ICl & chloramine-T. Isolation of
Carotenes-Purification by paper, TLC and Column. Charecterization of natural products by
oxidation studies, Derivatization of natural products.

OC P 509: Organic Chemistry Practicals – V

Separation, purification, analysis and derivatization of ternary mixture of organic compounds,
Identification, separation and qualitative analysis of the individual compounds and
preparation of suitable derivative for each component, identification of derivative by m.p.,
TLC and spectral techniques.

References:-
1. Elementary Practical Organic Chemistry-Vol. III: quantitative Organic Analysis- A.I
Vogel
2. Vogel’s Text Book of Practical Organic Chemistry- Furniss et al. (ELBS, London)1978.
3. Experimental Organic Chemistry- Vol. I &II- P.R.Singh (Tata McGraw-Hill) 1981.
4. Practical Organic Chemistry- IV Ed- Dey &.Sitaraman (Allied)
5. Laboratory Experiments in Organic Chemistry-Adam, Johnson & Wicon (McMillan,
London) 1979.
6. Experimental Organic Chemistry- H. D. Durst & G. E. Goke (McGraw-Hill)1980
 4th SEMESTER

OC H 551: Organic Synthetic Methods

UNIT-I: [15 Hours]

Reduction Reactions: Catalytic hydrogenation-Introduction, catalysts and solvents
employed, reduction of functional groups, mechanisms and stereochemistry of catalytic
hydrogenations, Hydrogenolysis, homogeneous catalytic hydrogenation.
Metal hydride reduction: Reduction with LiAlH4, NaBH4, BH3, AlH3 and DIBAL.
Stereochemistry of reduction, Functional group transformation during reduction, Reduction
with diborane and related reactions. Reduction with Trimethylsilane. Reduction in Biological
systems-NADH, FAD.
Dissolving Metal Reductions: Mechanisms of reduction of conjugated system and carbonyl
compounds((including Birch, Benkeser, Clemmensen reductions), Bimolecular reductions of
esters, Birch reduction, Reduction with hydrazine and its derivatives, Wolf-Kishner
reduction, McMurry reaction, Pummer, Willgerdot, Corey-Bakshi-Shibata and Tishchenko
reactions. Reduction with arene sulphonyl derivative of hydrazine, Reaction with diimide and
related compounds.

UNIT-II: [15 Hours]

Oxidation Reactions: Introduction and different oxidative processes, Mechanism of
oxidation reaction with chromium (Jones, Sarett, Collins & PCC), Lead tetra acetate, Oxone,
Osmium tetroxide, MnO2 and manganese salts, peracids and peresters, periodic acid, Ozone,
Dess-Martin periodinane, TEMPO, CAN, Swern oxidation and their synthetic importance in
functional group transformation.
Halogenation Reactions: Halogenation of olefins and carbonyl compounds, Benzylic and
Allylic halogenation, Dehalogenation reactions. Dehydrogenation with S, Se, Pt, Pd, Ni.

UNIT-III [15 Hours]

Basic principles and technologies used in disconnection approach. Synthons and synthetic
equivalents. Interconversion of functional groups. One group C-X and two group C-X
disconnections.
Protecting groups: Principle of protection of hydroxyl, amino, carboxylic and carbonyl
groups and their synthetic applications.
Retrosynthetic analysis: Analysis of alcohols, carbonyl compounds, cyclic and acyclic
alkanes, benzocaine, p-methoxyacetophenone, acetonecyanohydrin, 2-methyl-6-methoxy-
indole-3-acetic acid, 6-methylquinoline & 1-phenyl-4-p-methoxyphenyl-1,3-butadiene,
Limonene, Danishefsky’s pentalenolactone, Benziodarone, nitrofurazone, Warfarin and
Juvabione.

References :
1. Modern Organic Reactions- H.O.House
2. Organic Synthesis- R.E.Ireland (Prentice Hall India) 1969.
3. Art in Organic Synthesis- Anand, Bindra & Ranganath (Wiley) 1970.
4. Organic Synthesis a Disconnection Approach- Stuart
5. Advanced Organic Chemistry, IV ed., Part A & B- Carrey & Sundberg (Kluwer-
Academic) 2001.
6. Modern Methods of Organic Synthesis-N. Carruthers (Cambridge University), 1996.
7. Selected Organic Synthesis-Ian Fleming (John Wiley & Sons) 1973.
 OC H 552: Medicinal Chemistry
UNIT-I: [15 Hours]
Drugs: Introduction, Classification and nomenclature of drugs. Theories of drug action-
Occupancy theory, Rate theory, Induced fit theory and Perturbation theory. Analogues and
Prodrugs, Factors governing drug design. Rational approach to drug design, Variation method
of drug designing, tailoring of drugs, Physico-Chemical factors and biological activities.
Factors governing the ability of drugs, Isosterism and Bio-isosterism.
Antipyretic Analgesics: Classification, synthesis of Phenacetin, Aspirin, Cinchophen,
Phenazone and Mefenamic acid, mode of action.
General Anesthetics: Introduction and classification, synthesis of methoxyfluorane,
Thiopental sodium and Fentanyl citrate, Mode of action.
Local anesthetic: Introduction and classification, synthesis of benzocaine, α-Eucaine,
Lignocaine hydrochloride and Dibucaine hydrochloride, Mode of action.
UNIT-II: [15 Hours]
Cardiovascular drugs: Introduction, classification, Synthesis of Hydralazine, Methyldopa,
Diazoxide, Procainamide, Propranolol, Bretylium tosylate, Isoxsupurine, Prenylamine & their
mode of action.
Antimalarials: Introduction and classification, Synthesis of Chloroquine phosphate,
Pamaquine, Meparine hydrochloride, Proguanil hydrochloride, pyrimethanine and dapsone,
Mode of action.
Antineoplastic agents: Introduction and classification, Synthesis of Mechlorethamine
hydrochloride, Busalfan triethylenemelamine, Methotrexate, Mercaptopurinum and
Flurouracil, Mode of action.
Antiviral drugs: Introduction, classification, mechanism of action study of some
representative drugs like Methisazone, Idoxuridine, Amantidine hydrochloride.
UNIT-III: [15 Hours]
Vitamins: Introduction, Classification and Nomenclature-Source and Deficiency diseases,
Biological, functions of Vitamins, Study of Vitamin A1, Vitamin B1, B2 and B6, Vitamin H,
Vitamin C, Vitamin E, Vitamin K1.
Antibiotics: Introduction, Classification, Chemistry of Pencillin V, Cephalosporine C,
Streptomycin, Chloramphenicol and Tetracyclin.
Prostaglandins: Introduction, Nomenclature, Classification and Biological role of
Prostaglandins, Structural elucidation and stereochemistry of PGE1, PGE2 and PGE3. Total
synthesis of PGE1 (Corey’s method & Up John’s synthesis).

References:
1. Medicinal Chemistry- Ashutosh Kar (New Age.) 2005,
2. Medicinal Chemistry- G. R.Chatwal (Himalaya) 2002.
3. Natural Products Chemistry, Vol-I & II- G. R. Chatwal (Himalaya) 1990.
4. Principles of Drug Action, II ed.- A.G oldstein Lewis Arnold & Suner M. Kalman (Wiley
Int. Ed.)
5. Organic Chemistry, Vol I & II, I.L.Finar (Longmann ELBS, London) 1973.
6. Chemistry of Natural Products, Vol-I & II – O. P. Agarwal (Goel Gorakhpur) 1985.
76. Chemistry of Natural Products: A Unified Approach-N R Krishnaswamy (University
Press) 1999.
8. Chemistry of Natural Products-Sujata V. Bhat, B.A. Nagasampagi, Meenakshi Sivakumar
(Springer-Narosa) 2005.

OC H 553: Natural Products Chemistry

UNIT-I: [15 Hours]
Alkaloids: Definition, Classification and isolation of alkaloids, general methods of structural
determination of alkaloids, detailed study of structure elucidation, stereochemistry,
rearrangement, Synthesis and biogenesis of Papaverine, Adrenaline, Ephedrine, Piperine,
Cinchonine, Quinine, Morphine, Yohimbine, Reserpine and Lysergic acid.

UNIT- II: [15 Hours]

Terpenoids: Introduction, classification, isoprene rules, methods of structure determination.
Structural elucidation & synthesis of Geraniol, Menthol, α-Pinene, Camphor, Farnesol,
Zingiberene and α-Santonin, Vetivones, Caryophylene.
Diterpenoids: Abietic and Gibberillic acid.
Triterpenoids: Squalene and Phytol.
Carotenoides: Introduction and geometrical isomerization of Carotenes. Structure and
Synthesis of β-Carotene and Lycopene.

UNIT- III: [15 Hours]

Steroids: Introduction and Nomenclature of steroids, Blanc’s rule, Barbier-Wieland
degradation, Oppenauer oxidation, Diel’s hydrocarbon, Chemistry of Cholestrol, Ergosterol,
Vitamin-D, Stigmasterol & bile acids.
Steroidal hormones: Chemistry of Oestrone, esterdiol, estriol and their chemical
relationship. Progesterone, androsterone and testosterone - Structure and Synthesis of
Cortisone, Cortisol and Aldosterone. Transformations in steroids and hormones. Steroidal
oral contraceptives.

References:
1. Natural Products Chemistry Vol-I & II. G. R. Chatwal (Himalaya) 1990.
2. Chemistry of Natural Products – Vol-I & II – O. P. Agarwal (Goel) 1985.
3. Organic Chemistry, Vol-I & II- I. L. Finar (Longmann ELBS London), 2000.
4. Chemistry of Natural Products: A Unified Approach-N R Krishnaswamy (University
Press) 1999.
5. Chemistry of Natural Products-Sujata V. Bhat, B.A. Nagasampagi, Meenakshi Sivakumar
(Springer-Narosa) 2005.

OC S 554: Synthetic Polymers, Dyes and Pesticides

UNIT–I: [12 Hours]

Synthetic polymers: Classification and Nomenclature. Methods of polymerization,
Mechanism and Stereochemistry, Addition polymerization (Anionic, Cationic and Free
radical process), Condensation and Stepwise polymerization, Coordination polymerization,
Ring opening polymerization. Mechanism of co polymerization. Properties, Structure and
applications of Polythene, Polypropylene, PVC, Polystyrene & Acrylic polymers, Teflon,
polyesters, polyamides, Phenol-Formaldehyde resins, Urea-Formaldehyde resins, Epoxy
resins, Polyurethanes, Polycarbonates, Synthetic rubber. Structural features and manufacture
of natural rubber and Regenerated cellulose. Ziegler-Natta catalyst.
UNIT -II : [12 Hours]
Dyes: Introduction, modern theories of colour and chemical constitution. Classification of
dyes, methods of applying dyes to the fabrics. A general study of Azo dyes- Orange –II,
rosanthrene O, Naphthol blue black 6B, Mordant brown, Congo red, Methyl orange,
Chrysoidin G, Bismark brown.
Triphenylmethane dyes- Malachite green, Rosaniline, Crystal violet and Phenolphthalein;
Cyanin dyes- Ethyl Red, Cyanin blue and Quinaldine, Reactive dyes and Optical
brighteners-Tinapal and Blankophor.
Pigments: Fast violet, Lake red and Orange R.

UNIT - III : [12 Hours]

Insecticides: Introduction, classification, mode of action and synthesis of Methoxychlor,
chlordane, heptachlor, Hexachlorocyclohexane, Parathion, Diazenon, Sevin and Beygon.
Naturally occurring insecticides-pyrethroids-natural pyrethrins-isolation and structures,
synthetic pyrethroids.
Insect Pheromones: Introduction, Classification and use in insect pest control. Synthesis of
disparlure, grandisol, Periplanone-A & B and bomykol.
Fungicides: Introduction, Systemic fungicides-types & examples.
Herbicides: Introduction, study of sulfonyl ureas and heterocyclic sulphonamides.
Fumigants and repellants. Mechanism of action and toxicities of insecticides, fungicides and
herbicides.

References:
1. Polymer Science- V.R.Gowariker, N.V.Vishwanathan & T.Shridhar (Wiley Eastern) 2008.
2. Textbook of Polymer Science, 3rd Edition, Fred W. Billmeyer (Wiley) 1984.
3. A Textbook of Synthetic Dyes- O.D. Tyagi & M. Yadav (Anmol Publications) 2002.
4. Textbook of Dyes - A. Arora (Sonali Publications) 2009.
5. Synthetic Dyes – Vol-I – Venkataraman, 1999.
6. Synthesis and Chemistry of Agrochemicals, Vol I & II, ACS, Wahington.
7. Chemicals for Crop Protection and Pest Managements, M B Green, G.S. Hartley West,
Pergamon.
8. Chemistry of Insecticides and Fungicides, Sree Ramulu, Oxford & IBH, 1985.

OC S 555: Separation Techniques and Organometallic Chemistry

UNIT- I: [12 Hours]

Column Chromatography (CC): Construction and operation of column, choice of
adsorbents and eluents, techniques of elution, methods of detection, analytical and industrial
applications.
Paper Chromatography (PC): Definitions, theory and principle, techniques; one, two-
dimensional and circular PC, mechanism of separation, structure of cellulose and types of
paper, methodology, preparation of sample, choice of solvents, location of spots and
measurements of RF value, factors affecting RF values, advantages and applications.
Thin Layer Chromatography (TLC): Definition, mechanism, efficiency of TL plates,
methodology selection of stationary and mobile phases, preparation of plates. Spotting,
development, identification and detection, reproducibility of RF values, comparison of TLC
with high performance thin-layer chromatography, paper chromatography and column
chromatography. Qualitative and quantitative analysis.
UNIT- II: [12 Hours]
Gas chromatography (GC): Principle, comparison of GSC and GLC, instrumentation
columns pack and tubular, study of detectors-thermal conductivity. Flame ionization, electron
capture and mass spectrometry. Factors affecting the separation, applications.
High Pressure Liquid Chromatography (HPLC): Apparatus, pumps, column packing,
charecteristics of liquid chromatographic detectors-UV, IR, refractometer and fluorescences
detectors, advantages and applications.
Organometallic Compounds: Transition metal alkyls and aryls- types, routes of synthesis,
Nucleophilic and electrophilic cleavage of metal-carbon sigma bonded compounds. Alkane
activation. Transition metal to carbon multiple-bonded compounds- carbenes, carbynes,
synthesis, structural characteristics and reactivity. Transition metal hydrides – synthetic
routes, properties, structure and reactivity, synthetic applications.

UNIT - III: [12 Hours]

Transition metal-carbon pi complexes: Preparative methods, nature of bonding, structural
features of olefinic, acetylenic, allylic and η5- cyclopentadienyl and η6- benzene complexes.
Important reactions relating to nucleophilic and electrophilic attack on ligands.
Catalysis by organometallic compounds:16- and 18-electron rules, oxidative addition,
insertion, deinsertion and reductive elimination reactions.
Homogeneous catalysis by organometallics: Hydrogenation, hydrosilation, hydrocyanation
and isomerization of olefins, immobilisation of homogeneous hydrogenation catalysts,
hydrocarbonylation of olefins (oxo reaction-cobalt and rhodium oxo catalysts), carbonylation
of alcohols-Monsanto acetic acid process. Polymerization of olefins and acetylenes: Ziegler-
Natta catalyst systems. Fischer-Tropsch reaction, Water Gas Shift reactions.
Synthetic applications of organocuprates. Hydrozirconation, transmetallation reactions by
organonickels, carbonylation by metal carbonylates.

References:
1. Chromatography-E. Heftman (Ed), Part A and Part B, 5th ed. Elsevier, 1992.
2. Chromatography Today- D. F. Poole and S.K. Poole, Elsevier , 1991.
3. Principles of Instrumental Analysis-Skoog, Holler and Nieman, 5th ed. Saunders, 1998
4. Quantitative Analysis-R. A. Day and A. L. Underwood, 5th ed. Prentice-Hall, 1998.
5. Instrumental Methods of Chemical Analysis -B. K. Sharma, 19th ed, Goel, 2000.
6. Principles and Applications of Organotransition Metal Chemistry -J.P.Collman,
L.S.hegedus, J.R.Norton and R.G.Finke (University Science Books) 1987.
7. Organometallic Chemistry - R.C.Mehrotra and A.Singh (New Age International) 1999.
8. Organometallic Chemistry of Transition Metals-R.H.Crabtree (Wiley) 1999.

.
OC S 556: Organic Synthetic Strategies and Petrochemicals

UNIT- I: [12 Hours]

Polymer supported reagents in organic synthesis: Introduction, properties of polymer

support, advantages of polymer supported reagents and choice of polymers. Applications:
Substrate covalently bound to the support: Synthesis of oligosachcharides, Dieckmann
cyclisation. Preparation of polymer bound aldehyde and application in aldol and Wittig
reactions. Synthesis of polystyryl boronic acid and use in diol protection reaction. Reagent
linked to a polymeric material: Preparation of sulfonazide polymer and application in
diazotransfer reaction. Synthesis of polymer bound per acid and its applications. Polymer
supported catalytic reactions: Preparation of polymer supported AlCl3 and application in
etherification and acetal formation reactions.
Multicomponent Reactions: Studies on the mechanistic aspects and use of the Ugi, Passerini,
Biginelli, Hantzsch, Doebner-Miller, Jacobson, Barbier, Baylis-Hilmann and Mannich
reactions.

UNIT- II: [12 Hours]

Assymmetric Synthesis: The Chiral pool; Alpha amino acids in the synthesis of
Benzodiapines, Carbohydrates(Benzyl D-Mannose to Swainsonine) Preparation of tomolal
from D-mannitol, Felion-Ahn model and Cram’s chelation control. Enantiomeric excess and
its determination.
Chiral Auxiliaries: Oxazolidinones, Chiral sulfoxides in controlling the reduction of
ketones, Use of chiral Auxillaries in Diels-Alder and aldol reactions.
Chiral Reagents: BINOL, DIBAL, Tartarates, Lithium diamides.
Chiral Catalysts: Rhodium and Ruthenium catalysts with Chiral phosphine ligands like (R)-
BINAP, (R,R)-DIOP.
Asymmetric amplification and autocatalysis.

UNIT- III: [12 Hours]

Petrochemicals: Origin and formation of Petroleum, Composition of crude Petroleum and
natural gas, Petroleum refining, reforming, fractionation, cracking, knocking, octane and
cetane numbers. Ion, different types of petroleum products and their applications. Ignition
point, flash point and octane number. Manufacture of synthetic petrol - Bergius and Fischer
Tropsh processes.
Origin of coal, coal carbonisation, coal gasification and coal tar based chemicals. Chemistry
of coal conversions.
Manufacture of petrochemicals: Preparation of methanol, chlorinated methanes and carbon
disulphide from methane, Preparation of Ethyl chloride, ethanol, ethylene oxide from
ethylene, anufacture of the following from propylene - Isopropanol, cumene, glycerine and
acrylonitrile. Manufacture of vinyl chloride, chloroprene, acrylonitrile and acetaldehyde
from acetylene.

References:
1. Stereochemistry of Organic compounds-Nasipuri (New Age International).
2. Stereochemistry of Organic compounds-P.S. Kalsi (Wiley Eastern).
3. Organic chemistry- J. Clayden, N. Greeves, S. Warren and P. Wothers (Oxford University Press).
4. Stereochemistry of Organic compounds - E. Eliel and S.H. Wilen (John Wiley).
5. Art in Organic Synthesis- Anand, Bindra & Ranganath-(Wiley New Delhi), 1970.
6. Organic Synthesis a Disconnection Approach- Stuart Warren
7. Advanced Organic Chemistry-IV-Ed. Part A & B-F.J.Carrey & R.J.Sundberg (Kluwer)
2001.
8. Modern Methods of Organic Synthesis, 2nd edn.-N.Carruthers (Cambridge University),
1998.
9. Introduction to Petrochemicals, 2nd ed. - S. Maiti (Oxford and IBH) 2002.
10. Modern Petroleum Refining Processes, 4th ed.- B.K.B. Rao (Oxford and IBH) 2005.
11. Advanced Petroleum Refining, 1st ed., G.N. Sarkar (Khanna Publishers) 1998.
12. The Chemistry and Technology of Petroleum - S.G James (Marcel Dekker) 1991.
13. Chrotechnology: Industrial Synthesis of Optically active compounds-R. A. Sheldon, Marcel
Dekker) 1993.
14. Organic Chemistry- R. E. Ireland (Prentice-Hall India) 1975.
15. Principles and applications of asymmetric synthesis-G D Lin, Y M Li and A S C Chan
(Wiley Interscience) 2001.
17. Organic synthesis: Special techniques-V. K. Ahluwalia and R. Aggarwal (Narosa) 2003
18. Polymers as aids in Organic synthesis- N. K. Mathur, C. K. Narang and R. E. Williams
(Academic Press) 1980.

OC P 557 : Organic Chemistry Practicals –VI

Preparation of Ethyl resorcinol from Resorcinol, 3-Bromo-4-methyl benzaldehyde from p-
Toluedine, ε-Caprolactam from cyclohexanone, p-Aminobenzoic acid from p-Nitrotoluene, s-
Tribromobenzene from aniline, o-hydroxyacetophenone from phenol, Benzanilide from
Benzophenone, Benzylic acid from Benzoin, Benzopinacolone from Benzophenone, p-
Chlorotoluene from p-Toludine, 2,5-Dihydroxyacetophenone from Hydroquinone, 2,4-
Dinitrophenylhydrazine from Chlorobenzene, m-Nitrobenzoic acid from Benzoic acid, 2,4-
Dinitrophenol from Chlorobenzene, o-Aminobenzoic acid from Phthalic acid, 2-
Carbethoxycyclopentanone from Adipic acid, α-Acetylaminocinnamic acid from Glycine, p-
Aminoazobenzene from Aniline.
Synthesis of one derivative each of Furan, Indole, Pyrazole, Quinoline, Thiazole, Acridine,
Coumarin and Triazole containing heterocycles. Synthesis of Picric acid, Para red, Methyl
red, Methyl orange, Flourescein, Eosin, Indigo and dyeing of fabrics.

OC P 558: ORGANIC CHEMISTRY PRACTICALS-VII

Separation of components from mixture of organic compounds by fractional crystallization,

fractional distillation, adsorption, Paper, TLC and column chromatography. The purification
and characterization of organic compounds.
Determination of pKa values, molar extinction coefficients, keto-enol equilibrium, order of
reactions-SN1 and SN2 reactions, salt effect and effect of acidity on reaction rates.
Preparation and Estimation of aryloxyacetic acids, anilinoacetic acids, Carbohydrates,
Proteins.
Elucidation of structure of organic compounds using UV, IR, NMR and Mass spectra.
Locating an organic compound by reference to literature (Chemical Abstract).
Applications of computers in the study of conformation and geometry of some simple organic
molecules. Utility of Chem draw and Chem sketch.

References:
1. Elementary Practical Organic Chemistry-Vol. III quantitative Organic Analysis- A.I. Vogel
2. Vogel’s Text Book of Practical Organic Chemistry- Furniss et al. (ELBS)1978.
3. Experimetal Organic Chemistry- Vol. I &II- P. R. Singh (Tata McGraw-Hill) 1981.
4. Practical Organic Chemistry- IV Ed- Dey & Sitaraman (Allied)
5. Laboratory Experiments in Organic Chemistry-Adam, Johnson & Wicon (McMillan), 1979.
6. Experimental Organic Chemistry- H. D. Durst & G. E. Goke (McGraw-Hill) 1980.
7. More Spectroscopic Problems in Organic Chemistry-A.J. Baker et al.(Heyden) 1975.
8. Spectral Problems in Organic Chemistry- Davis & Wells (Chapman & Hall) 1984

OC P 559: PROJECT WORK AND DISSERTATION