T Y BSc Organic Chemistry 6 Units Sem V1 Syllabus Mumbai University

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T.Y.B.Sc, CHEMISTRY (Six Units)
SEMESTER V
ORGANIC CHEMISTRY
COURSE CODE: USCH503 CREDITS: 02 LECTURES: 60
Unit I
1.1 Mechanism of organic reactions (10 L)
1.1.1 The basic terms & concepts: bond fission, reaction intermediates, electrophiles & nucleophiles,
ligand, base, electrophilicity vs. acidity & nucleophilicity vs basicity.
1.1.2 Neighbouring group participation in nucleophilic substitution reactions : participation of lone
pair of electrons, kinetics and stereochemical outcome.
1.1.3 Acyl nucleophilic substitution (Tetrahedral mechanism): Acid catalyzed esterification of
carboxylic acids ( A AC2) and base promoted hydrolysis of esters ( B AC2).
1.1.4 Pericyclic reactions, classification and nomenclature
1.1.4.1 Electro cyclic reactions (ring opening and ring closing), cycloaddition, sigma tropic
Rearrangement, group transfer reactions, cheletropic reaction (definition and one example of
each type)
1.1.4.2 Pyrolytic elimination: Cope, Chugaev, pyrolysis of acetates
References:
1.A guidebook to mechanism in Organic Chemistry, 6th edition, Peter Sykes, Pearson education,
New Delhi
2.Organic Reaction Mechanism, 4th edition, V. K. Ahluwalia, R. K. Parashar, Narosa Publication.
3.Organic reactions & their mechanisms,3rd revised edition, P.S. Kalsi, New Age International
Publishers.
4.M.B.Smith and J. March, Advanced organic chemistry- reactions mechanism and structure,
5th edition.
1.2 Photochemistry (5 L)
1.2.1 Introduction: Difference between thermal and photochemical reactions. Jablonski diagram,
singlet and triplet states, allowed and forbidden transitions, fate of excited molecules,
photosensitization.
1.2.2 Photochemical reactions of olefins: photoisomerization, photochemical rearrangement of 1,4-
dienes (di- π methane)
1.2.3 Photochemistry of carbonyl compounds: Norrish I, Norrish II cleavages. Photo reduction (e.g.
benzophenone to benzpinacol)
References:
1.Organic Chemistry, 7th Edition, R.T. Morrison, R. N. Boyd & S. K. Bhattacharjee, Pearson.
2.Organic chemistry,8th edition, John Mc Murry
Unit II
2.1 Stereochemistry I (5 L)
2.1.1 Molecular chirality and elements of symmetry: Mirror plane symmetry, inversion center,
roation -reflection (alternating) axis.

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2.1.2 Chirality of compounds without a stereo genic center: cummulenes and biphenyls.
References:
1.L. Eliel , stereochemistry of carbon compounds, Tata McGraw Hill
2.Stereochemistry P.S.Kalsi , New Age International Ltd.,4th Edition
3.Stereochemistry by Nassipuri.
2.2 Agrochemicals (4 L)
2.2.1 General introduction & scope, meaning & examples of insecticides, herbicides, fungicide,
rodenticide, pesticides, plant growth regulators.
2.2.2 Advantages & disadvantages of agrochemicals
2.2.3 Synthesis & application of IAA ( Indole Acetic Acid) & Endosulphan,
2.2.4 Bio pesticides – Neem oil & Karanj oil.
References:
1. Insecticides & pesticides: Saxena A. B., Anmol publication.
2. Growth regulators in Agriculture & Horticulture: Amarjit Basra, CRC press 2000.
3. Agrochemicals and pesticides: A.Jadhav and T.V.Sathe.
2.3 Heterocyclic chemistry: (6 L)
2.3.1 Reactivity of pyridine-N-oxide, quinoline and iso-quionoline.
2.3.2 Preparation of pyridine-N-oxide, quinoline (Skraup synthesis) and iso-quinoline ( Bischler-
Napieralski synthesis).
2.3.3 Reactions of pyridine-N-oxide: halogenation, nitration and reaction with NaNH 2/liq.NH 3,
n-BuLi.
2.3.4 Reactions of quinoline and isoquinoline; oxidation,reduction,nitration,halogenation and
reaction with NaNH 2/liq.NH 3,n-BuLi.
References
1.Name Reactions in Heterocyclic Chemistry, Jie-Jack Li, Wiley-Interscience publications, 2005.
2.Handbook of Heterocyclic Chemistry, 2nd Edition, Alan R. Katritzky and Alexander F.
Pozharskii, Elsevier Science Ltd, 2000.
3.Heterocyclic Chemistry, 5th Edition, John A. Joule and Keith Mills, Wiley publication, 2010.
4.Heterocyclic chemistry, 3rd Edition, Thomas L. Gilchrist, Pearson Education, 2007.
Unit III
3.1 IUPAC (5 L)
IUPAC Systematic nomenclature of the following classes of compounds (including compounds upto
two substituents / functional groups):
3.1.1 Bicyclic compounds – spiro, fused and bridged (upto 11 carbon atoms) – saturated
and unsaturated compounds.
3.1.2 Biphenyls
3.1.3 Cummulenes with upto 3 double bonds
3.1.4 Quinolines and isoquinolines
References

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1.Nomenclature of Organic Chemistry : IUPAC recommendations and preferred Names 2013,
RSC publication.
2.IUPAC nomenclature by S.C.Pal.
3.2 Synthesis of organic compounds (10L)
3.2.1 Introduction: Linear and convergent synthesis, criteria for an ideal synthesis, concept of chemo
selectivity and regioselectivity with examples, calculation of yields.
3.2.2 Multicomponent Synthesis: Mannich reaction and Biginelli reaction. Synthesis with examples
(no mechanism)
3.2.3 Green chemistry and synthesis:
Introduction: Twelve principles of green chemistry, concept of atom economy and E-factor,
calculations and their significance, numerical examples.
i) Green reagents: dimethyl carbonate.
ii) Green starting materials : D-glucose
iii)Green solvents : supercritical CO 2
iv)Green catalysts: Bio catalysts.
3.2.4 Planning of organic synthesis
i) synthesis of nitroanilines. ( o&p)
ii) synthesis of halobenzoic acid.( o&p)
iii) Alcohols (primary / secondary / tertiary) using Grignard reagents.
iv) Alkanes (using organo lithium compounds)
Reference:
1.Green chemistry an introductory text : Mike Lancaster.
2.Green chemistry: V. K. Ahluwalia (Narosa publishing house pvt. ltd.)
3.Green chemistry an introductory text : RSC publishing.
4.New trends in green chemistry V. K. Ahluwalia , M. Kidwai, Klumer Academic publisher
5.Green chemistry by V. Kumar.
6.Organic chemistry: Francis Carey
7.Organic chemistry: Carey and Sundberg.
Unit IV
4.1 Spectroscopy I (5 L)
4.1.1 Introduction: Electromagnetic spectrum, units of wavelength and frequency
4.1.2 UV – Visible spectroscopy: Basic theory, solvents, nature of UV-Visible spectrum, concept of
chromophore, auxochrome, bathochromic and hypsochromic shifts, hyperchromic and
hypochromic effects, chromophore-chromophore and chromophore-auxochrome interactions.
4.1.3 Mass spectrometry: Basic theory. Nature of mass spectrum. General rules of fragmentation.
Importance of molecular ion peak, isotopic peaks, base peak, nitrogen rule, rule of 13 for
determination of empirical formula and molecular formula. Fragmentation of alkanes and
aliphatic carbonyl compounds.
References:
1.Organic spectroscopy (Second edition),Jag Mohan ,Narosa publication
2.Spectroscopy, Pavia, Lampman, Kriz,Vyvyan.

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3.Elementary organic spectroscopy (Third edition), Y.R.Sharma, S.Chand publication..
4.Introduction to spectroscopy (third edition), Pavia ,Lampman,Kriz,john vondeling,Emily
Barrosse.
5.Organic chemistry Paula Y. Bruice, Pearson education.
6.Spectral identification of organic molecules by Silverstein.
7.Absorption spectroscopy of organic molecules by V.M.Parikh.
4.2 Natural Products: (10L)
4.2.1. Terpenoids: Introduction, Isoprene rule, special isoprene rule and the gem-dialkyl rule.
4.2.2 Citral:
a)Structural determination of citral.
b)Synthesis of citral from methyl heptenone
c)Isomerism in citral. (cis and trans form).
4.2.3. Alkaloids Introduction and occurrence.
Hofmann’s exhaustive methylation and degradation in: simple open chain and N – substituted
monocyclic amines.
4.2.4 Nicotine:
a)Structural determination of nicotine. (Pinner’s work included )
b)Synthesis of nicotine from nicotinic acid
c)Harmful effects of nicotine.
4.2.5 Hormones:
Introduction, structure of adrenaline (epinephrine), physiological action of adrenaline.
Synthesis of adrenaline from
a)Catechol
b)p-hydroxybenzaldehyde( Ott’s synthesis)
References:
1.Chemistry of natural products by Chatwal Anand – Vol I and Vol II
2.Chemistry of natural products by O.P. Agarwal
3.Chemistry of natural products by Meenakshi Sivakumar and Sujata Bhat.
4.Organic chemistry by Morrision and Boyd,7th edition.
5.I.L.Finar,Vol-I and Vol-II, 5th edition.
PRACTICALS
SEMESTER V
ORGANIC CHEMISTRY
COURSE CODE: USCHP09 CREDITS: 02
A)SEMESTER V : Separation of Binary solid-solid mixture (2.0 gms mixture to be given).
1. Minimum Six mixtures to be completed by the students.
2. Components of the mixture should include water soluble and water insoluble acids (carboxylic
acid), water insoluble phenols( 2-naphthol, 1-naphthol), water insoluble bases

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(nitroanilines) , water soluble neutral (thiourea) and water insoluble neutral compounds (anilides ,
amides, m-DNB, hydrocarbons)
After correct determination of chemical type, the separating reagent should be decided by the student
for separation.
4. Follow separation scheme with the bulk sample of binary mixture.
5. After separation into component A and component B, one component (decided by the examiner) is
to be analyzed and identified with m.p..
References:
1.Practical organic chemistry – A. I. Vogel
2.Practical organic chemistry – H.Middleton.
3.Practical organic chemistry – O.P.Aggarwal.
SEMESTER VI
ORGANIC CHEMISTRY
COURSE CODE: USCH603 CREDITS: 02 LECTURES: 60
Unit I
1.1 Stereochemistry II (10 L)
1.1.1 Stereoselectivity and stereospecificity: Idea of enantioselectivity (ee) and diastereoselectivity
(de) , Topicity : enantiotopic and diasterotopic atoms, groups and faces.
1.1.2 Stereochemistry of –
i) Substitution reactions : S Ni (reaction of alcohol with thionyl chloride)
ii) Elimination reactions: E 2–Base induced dehydrohalogenation of 1-bromo-1,2-
diphenylpropane.
iii) Addition reactions to olefins:
a) bromination (electrophilic anti addition)
b) syn hydroxylation with O sO4 and KMnO 4
c) epoxidation followed by hydrolysis.
References:
Refer Stereochemistry –I (Sem-V, Unit-II)
1.2 Amino acids & Proteins (5 L)
1.2.1 α-Amino acids: General Structure, configuration, and classification based on structure and
nutrition. Properties: pH dependency of ionic structure, isoelectric point and zwitter ion. Methods
of preparations: Strecker synthesis, Gabriel phthalamide synthesis.
1.2.2 Polypeptides and Proteins: nature of peptide bond. Nomenclature and representation of
polypeptides (di-and tri-peptides) with examples Merrifield solid phase polypeptide synthesis.
.Protiens:general idea of primary,secondary,tertiary & quaternary structure

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References:
1.Biochemistry, 8th Ed., Jeremy Berg, Lubert Stryer, John L. Tymoczko, Gregory J. Gatto Pub. W.
H. Freeman Publishers
2.Lehninger Principles of Biochemistry 7th Ed., David Nelson and Michael Cox, Publisher W. H.
Freeman
3.Name Reactions – Jie Jack Li, 4th Edition, Springer Pub.
Unit II
2.1 Molecular Rearrangements (5 L)
Mechanism of the following rearrangements with examples and stereochemistry wherever applicable.
2.1.1 Migration to the electron deficient carbon: Pinacol-pinacolone rearrangement.
2.1.2 Migration to the electron deficient nitrogen: Beckmann rearrangement.
2.1.3 Migration involving a carbanion : Favorski rearrangement.
2.1.4 Name reactions: Michael addition, Wittig reaction.
References:
Refer Mechanism of organic reaction (Sem-V, Unit-I)
2.2Carbohydrates (10 L)
2.2.1 Introduction: classification, reducing and non-reducing sugars, DL notation
2.2.2 Structures of monosaccharides: Fischer projection (4-6 carbon monosaccharides)
and Haworth formula (furanose and pyranose forms of pentoses and hexoses)
Interconversion: open chain and Haworth forms of monosaccharides with 5 and 6 carbons.
Chair conformation with stereochemistry of D-glucose, Stability of chair form of D-glucose
2.2.3 Stereoisomers of D-glucose: enantiomer, diastereomers, anomers, epimers.
2.2.4 Mutarotation in D-glucose with mechanism
2.2.5 Chain lengthening & shortening reactions: Modified Kiliani-Fischer synthesis (D-arabinose to
D-glucose and D-mannose), Wohl method (D-glucose to D-arabinose)
2.2.6 Reactions of D-glucose and D-fructose:
(a)Osazone formation (b) reduction: Hi/Ni, NaBH 4 (c) oxidation: bromine water, HNO 3, HIO 4
(d) acetylation (e) methylation:(d) and (e) with cyclic pyranose forms
2.2.7 Glycosides: general structure
References:
1.Organic chemistry (fourth edition),G,Marc Loudon,Oxford University press.
2.Introduction to Organic Chemistry (Third edition), Andrew Streitwieser, Jr. Clayton H.
Heathcock, Macmilan publishing.
3.Organic chemistry fourth edition, Morrision and Boyd.
4.Introduction to Organic chemistry,John McMurry.
5.Organic chemistry volume-1&2 (fifth and sixth edition) IL Finar.
Unit III
3.1 Spectroscopy II (10 L)
3.1.1 IR Spectroscopy: Basic theory, nature of IR spectrum, selection rule, fingerprint region.
3.1.2 PMR Spectroscopy: Basic theory of PMR, nature of PMR spectrum, chemical shift (  unit),
standard for PMR, solvents used. Factors affecting chemical shift: (1) inductive effect (2)
anisotropic effect (with reference to C=C, C≡C, C=O and benzene ring). Spin- spin coupling and

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coupling constant. application of deuterium exchange technique. application of PMR in structure
determination.
3.1.3 Spectral characteristics of following classes of organic compounds, including benzene and
monosubstituted benzenes, with respect to IR and PMR: (1) alkanes (2) alkenes (3) alkynes (4)
haloalkanes (5) alcohols (6) carbonyl compounds (7) ethers (8) amines (broad regions
characteristic of different groups are expected).
Problems of structure elucidation of simple organic compounds using individual or combined use
of UV-Vis, IR, Mass and NMR spectroscopic technique are expected. (Index of hydrogen
deficiency should be the first step in solving the problems).
References:
Refer spectroscopy –I, (Sem-V, Unit-IV)
3.2 Nucleic Acids (5 L)
Controlled hydrolysis of nucleic acids. sugars and bases in nucleic acids. Structures of
nucleosides and nucleotides in DNA and RNA. Structures of nucleic acids (DNA and RNA)
including base pairing.
References:
1.Organic chemistry R.T.Morrison and R.N.Boyd, 6th edition, pearson education
2.S.H.Pine, organic chemistry 4th edition. McGraw Hill
Unit IV
4.1 Polymer (8 L)
4.1.1 Introduction: terms monomer, polymer, homopolymer, copolymer, thermo
plastics and thermosets.
4.1.2 Addition polymers: polyethylene, polypropylene, teflon, polystyrene, PVC, Uses.
4.1.3 Condensation polymers: polyesters, polyamides, polyurethanes, polycarbonates, phenol
formaldehyde resins.Uses
4.1.4 Stereochemistry of polymers: Tacticity, mechanism of stereochemical control of polymerization
using Ziegler Natta catalysts.
4.1.5 Natural and synthetic rubbers: Polymerisation of isoprene: 1,2 and 1,4 addition
(cis and trans), Styrene butadiene copolymer.
4.1.6 Additives to polymers: Plasticisers, stabilizers and fillers.
4.1.7 Biodegradable polymers: Classification and uses. polylactic acid structure, properties and
use for packaging and medical purposes.
(Note : Identification of monomer in a given polymer & structure of polymer for a given
monomer is expected. condition for polymerization is not expected)
References:
1.Polymer chemistry by M.G.Arora, K.Singh.
2.Polymer science – a text book by Ahluwalia and Mishra
3.Introduction to polymer chemistry - R.Seymour, Wiley Interscience.
4.2 Catalysts and Reagents (7 L)
Study of the following catalysts and reagents with respect to functional group transformations
and selectivity (no mechanism).
4.2.1 Catalysts: Catalysts for hydrogenation:
a.Raney Nickel

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b.Pt and PtO 2 ( C=C, CN, NO 2, aromatic ring)
c.Pd/C : C=C, COCl→CHO (Rosenmund)
d.Lindlar catalyst: alkynes
d.2.2 Reagents :
a.LiAlH 4 (reduction of CO, COOR, CN,NO 2)
b.NaBH 4 (reduction of CO)
c.SeO 2 (Oxidation of CH 2 alpha to CO)
d. mCPBA (epoxidation of C=C)
e.NBS (allylic and benzylic bromination)
References:
1.Organic chemistry by Francis Carey – McGrawHill .
2.Oranic chemistry by Carey and Sundberg, Part A & B
PRACTICALS
SEMESTER VI
ORGANIC CHEMISTRY
COURSE CODE: USCHP10 CREDITS: 02
A)SEMESTER VI: Separation of Binary liquid-liquid and liquid- solid mixture.
1.Minimum Six mixtures to be completed by the students.
2.Components of the liq-liq mixture should include volatile liquids like acetone, methylacetate,
ethylacetate, isopropylalcohol, ethyl alcohol, EMK and non volatile liquids like chlorobenzene ,
bromobenzene, aniline, N,N dimethylaniline, acetophenone, nitrobenzene, ethyl benzoate.
3.Components of the liq- solid mixture should include volatile liquids like acetone, methylacetate,
ethylacetate, ethyl alcohol, IPA, EMK and solids such as water insoluble acids, phenols, bases,
neutral.
4.A sample of the mixture one ml to be given to the student for detection of the physical type of the
mixture.
5.After correct determination of physical type, separation of the binary mixture to be carried out by
distillation method using microscale technique.
6.After separation into component A and component B, the compound to be identified can be decided
by examiner.
References:
4.Practical organic chemistry – A. I. Vogel
5.Practical organic chemistry – H.Middleton.
6.Practical organic chemistry – O.P.Aggarwal.
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