Title: Organic Chemistry-II (Code-09040203)
|S.No.||Topic||Domain||Hours as per UGC|
|1||Unit-1 The SN2, SN1, mixed SN1 and SN2, SNi , SN1’, SN2’ SNI’ and SET mechanisms. The neighbouring group mechanisms, neighbouring group participation by p and s bonds, anchimeric assistance.||Must Know||12|
|Classical and non-classical carbocations, phenonium ions, common carbocation rearrangements.|
|Application of NMR spectroscopy in the detection of carbocations.||Desirable to know|
|Reactivity- effects of substrate structure, attacking nucleophile, leaving group and reaction medium. Ambident nucleophile, regioselectivity. Phase transfer catalysis.||Must know|
|2||Unit -2 Bimolecular mechanisms – SE2 and SEi. The SE1 mechanism, Electrophilic substitution accompained by double bond shifts. Effect of substrates, leaving group and the solvent polarity on the reactivity.||Must Know||10|
|The arenium ion, mechanism, orientation and reactivity, energy profile diagrams.|
|The ortho/para ratio, ipso attack, orientation in other ring systems. Quantitative treatment of reactivity in substrates and electrophiles. Diazonium coupling, Vilsmeir reaction, Gattermann-Koch reaction.|
|The ArSN1, ArSN2, Benzyne and SRN1 mechanisms. Reactivity –||Nice to know|
|effect of substrate structure, leaving group and attacking nucleophile. The von Richter, Sommelet-Hauser, and Smiles rearrangements.|
|3||Unit- 3 The E2, E1 and E1cB mechanisms . Orientation of the double bond . Reactivity –effects of substrate structures, attacking base, the leaving group and the medium. Mechanism and orientation in pyrolytic elimination.||Must Know||12|
|Mechanistic and stereochemical aspects of addition reactions involving electrophiles, nucleophiles and free radicals, regio – and chemoselectivity, orientation and reactivity. Addition to cyclopropane ring|
|Hydrogenation of double and triple bonds, hydrogenation of aromatic rings. Hydroboration. Michael reaction. Sharpless asymmetric epoxidation.||Desirable to know|
|4||Unit – 4||Must Know||7|
|Mechanism of metal hydride reduction of saturated and unsaturated carbonyl compounds, acids, esters and nitriles. Addition of Grignard reagents, organozinc and organolithium reagents to carbonyl and unsaturated carbonyl compounds.|
|Wittig reaction. Mechanism of condensation reactions involving enolates – Aldol, Knoevenagel, Claisen, Mannich, Benzoin, Perkin and Stobbe reactions. Hydrolysis of esters and amides, ammonolysis of esters.|
1. March, Jerry. Advanced Organic Chemistry Reactions, Mechanism and Structure.
2. Carey, F.A. and R.J. Sundberg. Advanced Organic Chemistry. Plenum.
3. Sykes, Peter. A Guide Book to Mechanism in Organic Chemistry.
4. Ingold, C.K. Structure and Mechanism in Organic Chemistry.
5. Morrison, R.T. and R.N. Boyd. Organic chemistry.
6. Benjamin, H.O. House. Modern Organic Reactions.
7. Norman, R.O.C. and J.M. Coxon. Principles of Organic Synthesis.
8. Mukherji, S.M. Pericyclic Reactions.
9. Mukherji, S.M. and S.P. Singh Reaction Mechanism in Organic Chemistry.