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PAPER I ORGANIC CHEMISTRY - I Subject Description : This contents of this paper present the basic principles of understanding mechanism of organic reactions. In addition to the general physical methods of approaching the course of reactions, specific examples like aromatic electrophilic substitution, aliphatic nucleophilic substitution, elimination and free radical reactions have been dealt with in detaiI. And also it gives a concise idea of concerted reactions, addition reactions, mechanism in organic photochemical reactions, elimination reactions and stereoisomerism in organic compounds. Goals : To motivate and enable the students to comprehend the possible chemical route by which a reaction may proceed and learn pericyclic reactions. A comprehensive knowledge on conformational analysis is also aimed. Objectives : On successful completion of the course the students should have: understood aromaticity, antiaromaticity and nonaromaticity in organic compounds, learnt possible reaction pathways in aromatic electrophilic, aliphatic nucleophilic, elimination and free radical reactions. mastered concerted reactions, Woodward-Hofmann rules, organic photochemistry, and stereoisomerism in organic compounds. Contents:

UNIT-I 1. Aromaticity : Introduction - Aromaticity of benzenoids and heterocyclic compounds. Non-benzenoid aromatics - annulenes. Azulenes and ferrocenes(synthesis not necessary). Antiaromatic and non aromatic compounds. 2. Kinetic and nonkinetic methods of study of reaction mechanisms - Kinetic methods primary and secondary kinetic isotopic effects, non-kinetic methods - study of reaction mechanism — study of intermediates, isotopic labeling, stereochemical studies and cross over experiments. Hammond’s postulate. Kinetic and thermodynamic control. 3. Linear free energy relationship — Hammett equation (Taft equation not necessary).

UNIT—Il Aromatic electrophilic substitution. reactions – Introduction - Mechanism of electrophilic substitution. reactions such as halogenation, nitration, sulphonation and Friedel – Crafts alkylation and acylation reactions. Orientation and reactivity. Electrophilic substitution on monosubstituted and disubstituted benzenes. Typical reactions such as Gattermann reaction Gattermann Koch reaction. Rimer Tiemann reaction. Kolbe reaction. Hofmann-Martius and Jacobson’s reactions.

UNIT-III Aliphatic nucleephilic substitution reactions & mechanisms: SNI, SN2, SNi mechanisms. Factors affecting nucleephilic substitution reaction – nature of the substrate, solvent, nucleophile and leaving group. Neighbouring group Anx.23 D - M Sc Chemistry (SDE) 2007-08 Page 3 of 16 participation. Ambident nucleophiles and ambident substrates. Stereochemistry of nucleophilic substitution reactions. Substitution at vinyl carbon allylic carbon and bridge head carbon. Typical substitutions such as Von Braun reaction, Claisen condensation and hydrolysis of esters.

UNIT- IV Elimination reactions: El, E2, Ei, E1CB mechanisms, Stereochemistry of elimination reactions. Elimination Vs substitution. Typical elimination reactions such as Chugaev reaction. Hofmann degradation. Cope elimination. Carbenes and nitrenes — structure, generation and reactions.

UNIT-V Free radical reactions: Introduction -structure, stability and geometry of free radicals. Generations of long lived and short lived free radicals. Characteristics of free radical reactions - substitutions - additions and eliminations, rearrangements. of free radicals. Typical reactions such as Sandmeyar, Gamberg, Pechmann, Ullman, Pschorr and Hunsdiecker reactions.

UNIT-VI 1. Additon reactions : Eelectrophilic and nucleophilic. Addition to double and triple bends — Hydration. hydroxylation. Michael addition. hydroboration and apoxidation. 2. Addition to carbonyl compounds : Mannich reaction, Dieckmann, Stobbe, Knovenagel, Darzen, Wittig, Thorpe and Benzoin reactions.

UNIT—VIl Concerted reactions: Pericyclic reactions — the perturbation theory of pericyclic reactions, the electrocyclic reactions & sigmatrophic reactions, the woodward — Hofmann rules, orbital correlation diagrams, the frontier orbital theory. Cycloadditions - Diel’s Alder reaction. Cope, Claisen and Di-pi - methane rearrangements.

UNIT - VIII Stereoisomerism – Configurational & conformational isomerism: Introduction, definition & classification. Molecular representation (Fischer projection, Newmann projection formula). Basic requirements of optical isomerism. Optical isomerism exhibited by a few nitrogen and sulphur compounds – the role of nitrogen inversion. Configurational nomenclature: D & L, R & S and E & Z(olefins) nomenclatures. Conformations of acyclic and cyclic molecules: Conformations of ethane and 1, 2 disubstituted ethanes. Configurations and conformations of cyclohexane, mono and disubstituted cyclohexanes(conformational equilibrium – delta G). Configurations and conformations of fused polycyclic systems – decalin, perhydrophenanthrene, perhydroanthracene. Anx.23 D - M Sc Chemistry (SDE) 2007-08 Page 4 of 16 PAPER IV - ORGANIC CHEMISTRY - II (Organic Synthesis and Natural Products) Subject Description : This paper gives a concise idea of molecular rearrangements, organic photochemistry, oxidation-reduction reactions, organic synthesis and synthetic reagents. This paper deals with chemistry of natural products – terpenoids, steroids, alkaloids, proteins and heterocyclic compounds. Goals : To enable the students to know molecular rearrangements, organic photochemistry organic synthesis and synthetic reagents, the chemical compositions of natural substances around them and to motivate them device synthetic routes to prepare natural products in the laboratory. Objectives : On successful completion of the course the students should have: mastered rearrangement reactions, Woodward-Hofmann rules, organic photochemistry, synthetically important name reactions in organic chemistry and synthetic reagents. understood the composition of the important natural materials around them. learnt scientific methods to synthesise organic natural products. Contents

UNIT - I Molecular rearrangements: Introduction - Wagner - Meerwein rearrangements, Neber rearrangement, Baeyer — villiger rearrangement. Rearrangements to electron deficient nitrogen and oxygen — Dienone phenol, Favorski, Fries, Wolt Benzidine and Stevens rearrangement.

UNIT - II 1. Organic photochemistry: Introductory theory of light absorption, photophysical processes, energy transfer photochemical reaction of ketones Norrish type I and type II reactions. Paterno – Buchi reaction and cis and trans isomerisation. 2. Oxidation and reductions: Mechanisms — aromatisation, oxidation of olefins, alcohols and glycols, ozonolysis,aromatization reaction and Sommelet reaction. Reduction reactions and selectivity in reduction. Reduction reactions involving metal hydrides(LiAlH4 and NaBH4). Reduction of nitro compounds, carbonyl compounds and aromatic compounds. Typical reactions such as Birch reduction, Clemmensen, Wolff – Kishner and MPV reduction.

UNIT I
II

1. Reactions and reagents: Reactions in organic synthesis: Oppanauer oxidation, Barbier – Wieland degradation, Barton reaction, Jones oxidation and Vilsmeier reaction. Anx.23 D - M Sc Chemistry (SDE) 2007-08 Page 10 of 16 2. Preparations and synthetic applications of DDQ(2,3-dichloro-5,6-dicyano-1,4- benzoquinone),DBU(1,5-diazabicyclo[5.4.0]undecene-5), CC(dicyclohexylcarbodiimide and crown ethers.

UNIT-IV Terpenes: Isolation and classification of terpenes — structural eIucidation and synthesis of zingiberene. eudesmol. juvenile hormone. abeitic acid and caryophyllene.

UNIT-V Steroids: Introduction — structural elucidation and synthesis of cholesterol, ergosterol, equilenin, estrone, testosterone and progesterone.

UNIT-VI Alkaloids: Introduction – Introduction, isolation of alkaloids, structural elucidation and synthesis of morphine, reserpine. quinine. Atropine and glaucine.

UNIT-VII 1. Proteins and nucleic acids: Classification and characteristics(structure) of proteins — synthesis of polypeptides and oxytocin, enzymes and coenzymes. Structure of RNA and DNA and their biological importance. 2. Heterocyclic compounds: Structure, synthesis and reactions of flavones, isoflavones, purines (Adenine and Guanine) and anthocyanins (Cyanin and Pelargonin).

UNIT VIII Mass spectroscopy and circular dichroism. 1. Principles of mass spectrometry - presentation and analysis of spectra-determination of molecular formulae-nitrogen rule-isotope abundance analysis-meta stable ions and peaksthe molecular ion peak-fragmentation processes-symbolism (scission only)-even and odd electron ions- double bond and or ring equivalents implied from a formula. 2. Applications of mass spectroscopy - Scission with rearrangement – retro Diels-Alder rearrangement – McLaffertty rearrangement –-fragmentation associated with functional groups - aldehydes and ketones-carboxylic acids, esters, amides, alcohols - aliphatic compounds - aromatic compounds 3. Circular dichroism and optical rotatory dispersion-basic principles-basic principles of O.R.D. and C.D.-cotton effects-Octants rule-axial halo ketone rule-application of O.R.D. and C.D.

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