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Course Detail

Course Name Frontiers in Organic Chemistry
Course Code 25CHY404 CORE COURSE
Program B.Sc. (Hons) in Chemistry
Semester 7
Credits 4
Campus Amritapuri , Coimbatore

Syllabus

Unit 1:

Pericyclic Reactions I[12 h]Molecular orbital symmetry. Frontier orbitals of ethylene, 1,3-butadiene, 1,3,5-hexatriene and allyl system. Classification of pericyclic reactions. Electrocyclic reactions con rotation and dis rotation in 4n, 4n+2, allyl systems and secondary effects. Electrocyclization of charged species and heteroatomic trienes.

Unit 2:

Pericyclic Reactions II[14 h]Cycloaddition reactions – antrafacial and suprafacial additions, 4n and 4n+2 systems with (2+2) and (4+2) cycloadditions. Effect of stereochemistry and substituents on the rate of cycloadditions, 1,3-dipolar cycloadditions and cheleotropic reactions. Sigmatropic rearrangements – suprafacial and antrafacial shifts – [1,2]-sigmatropic shifts involving carbon moieties. [m,n] and [m,m] sigmatropic hydrogen shifts. Claisen, Cope, Wittig and azaWittig rearrangements, fluxional tautomerism. Ene reactions.

Unit 3:

Photochemistry I[10 h]Photochemistry of alkenes- intramolecular reactions, geometrical isomerism, cyclisation reactions. Photochemical rearrangements – 1,4 and 1,5- dienes. Photochemistry of aromatic compounds – isomerizations, additions, substitutions and photo reduction.

Unit 4:

Photochemistry II[14 h]Photochemistry of carbonyl compounds – Norrish type I and type II, and PatternoBuchi reactions. Intramolecular reactions of carbonyl compounds saturated cyclic and acyclic, ?,? and ?,?- unsaturated compounds, cyclohexanone, cyclohexadienones. Intermolecular cycloaddition reactions and dimerisations. Photo-Fries reactions and rearrangements, Lumiketone rearrangement and Barton reaction. Photo reduction of carbonyl compounds. Singlet molecular oxygen reactions. Photostabilizers.

Unit 5:

Heterocyclic Compounds [10 h]Biologically important heterocycles, Hantzsch-Widman system for monocyclic, fused and bridged heterocycles. Aromaticity of one, two, three, four, five, six and fused heterocycles. Physical and Chemical properties of various heterocyclic compounds.

Evaluation Pattern

CO1: Explore various light induced reactions in organic chemistry.

CO2: Apply the basic principles of bonding in ground state and excited state to establish different reaction mechanisms.

CO3: Analyze the effect of energy transfer on the different reaction mechanisms.

CO4: Explain reaction mechanism with the help of molecular orbital theory.

CO5: Elucidate the synthesis of different bioactive molecules.

Text Books / References

Recommended Readings

1.Carey, F.A. and Sundberg, R.J., 2007. Advanced organic chemistry: part A: structure and mechanisms. Springer Science & Business Media.

2.Carey, F.A. and Sundberg, R.J., 2007. Advanced organic chemistry: part B: reaction and synthesis. Springer Science & Business Media.

3.Smith, M.B., 2020. March’s advanced organic chemistry: reactions, mechanisms, and structure. John Wiley & Sons.

4.Sankararaman, S., 2005. Pericyclic Reactions-A Textbook: Reactions, Applications and Theory. Wiley-VCH.

5.Singh, N.D., 2014. Organic photochemistry and pericyclic reactions.

6.Kln, P. and Wirz, J., 2009. Photochemistry of organic compounds: from concepts to practice. John Wiley & Sons.

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