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Indian Institute of Technology, Kharagpur

Structure Stereochemistry And Reactivity Of Organic Compounds And Intermediates: A Problem-solving Approach

Indian Institute of Technology, Kharagpur and NPTEL via Swayam

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Organic chemistry has been synonymous with Chemistry of Carbon Compounds (other than simple salts, oxides and carbides). Besides carbon, organic compounds are mainly made of hydrogen, nitrogen, oxygen, phosphorous and smaller amounts of a few other elements and are thus distinct from other materials. Most of the mass in living things is made up of organic compounds. Unlike various branches of science including physical chemistry where many problems involve determining appropriate equations and solving them, students have a hard time adjusting to organic chemistry, which has its own logic that cannot be mastered by going through in bits and pieces. Only after having gone through the various classes of organic molecules and their reactive sites, one can start seeing the correlation between the different classes of organic reactions and their mechanistic details. The purpose of this course entitled Structure, Stereochemistry and Reactivity of Organic Compounds and Intermediates: A Problem-solving Approach is to provide a solid foundation on organic chemistry through a problem solving technique which centers on structure, stereochemistry and a mechanistic approach. Completion of this course enables the students to arrive at the realization that organic chemistry can not only be mastered, but is enjoyable as well. INTENDED AUDIENCE :Chemistry, Biochemistry, Biotechnology, Pharmacy undergraduate students PREREQUISITES : Preferably taken a basic Organic Chemistry course at the first UG level and also the Stereochemistry course by NPTELINDUSTRIES SUPPORT :Speciality Chemical and Pharmaceutical Companies


Week 1:Structure and stereochemistry :A brief introduction to different types of chirality: Tetrahedral, Axial, Planar, Helical including assignment of absolute configuration. Pseudoasymmetry and Reflection Invariance Issue. Week 2:Conformations of saturated fused ring systems (decalins), heterocycles (sugars) and polynuclear hydrocarbons (perhydrophenanthrene, anthracene and steroid) Week 3:3D Structure determination of Chiral Molecules: Chiroptical properties: ORD and CD; Cotton effect; axial haloketone and octant rules; determination of conformation and configuration Week 4:Stereoelectronic control on conformation and reactivity; Intramolecular Cyclizations: Baldwin rules
Week 5:Organic Intermediates : Alkynes, Arynes, Allenes, Ketenes and methods of their generation, structures and reactivity Week 6:Organic Intermediates : C-Radicals: structure and stability; classification: nucleophilic, electrophilic and captodative; inter and intramolecular additions to C=C, CΞC. CΞN, C=NOH; Umpolung reactions; Barton reactionWeek 7:Asymmetric Reactions of Carbonyls: Stereochemistry of nucleophilic addition to carbonyls and unsaturated carbonyls; Asymmetric alkylation Week 8:Asymmetric Reactions of Carbonyls : Aldol reactions: Zimmerman-Traxler model, chiral auxiliary and catalytic approaches

Taught by

Prof. Amit Basak



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