1. Disconnection approach
Introduction to synthons, and synthetic equivalents, disconnection approach. Basic principles and terminologies used in the disconnection approach. Designing of a synthesis, consider a range of possibilities, the availability, starting materials & equipment, Convergent & Linear synthetic approach, Yield & Conversion, Use of Inherent Symmetry. One group C-X and two group C-X disconnections. Chemoselectivity, reversal of polarity, cyclisation reactions.
Functional group interconversion and protecting groups.
Introduction, Functional group interconversion (FGIs), Carboxylic acid and its derivatives, Aldehydes, Ketones and their derivatives, Alcohols and their derivatives, Oxidation & Reductions, Removal of functional groups, Protecting groups, Protection of alcohols, Acetals, Ethers, Trialkylsilyl ether, Protection of aldehydes and ketones, Protection of amino acids, Protection of sugars and solved examples.
C-C one group and C-C two group disconnections
Synthesis of alcohols, carbonyl compounds, and alkenes. Use of acetylides and aliphatic nitro compounds in organic synthesis. Diels-Alder reaction, 1,3-functionalised compounds, α,β- unsaturated compounds, carbonyl compounds condensations, 1,5- functionalised compounds. Micheal addition and Robinson annelation.
Synthesis of saturated heterocycles and 3-, 4-, 5- and 6-membered rings.
Synthesis of some complex molecules using disconnection approach
Aromadendrene, longifloene, cortisone, reserpine, vitamin-D, juvabione, fredericamycin-A and Lycorane.
2. Molecular Orbital Symmetry
Introduction to molecular orbital symmetry (Woodward and Hofmann Rules), Huckel molecular orbitals for ethylene, and conjugated polyenes. Reactions obeying Woodward Hofmann rules.cycloaddition, electrocyclic and sigmatropic reactions.
1. With the help of this course, students will acquire knowledge of the mechanistic pathway of organic reactions and the retrosynthetic approach to planning organic syntheses. To make students aware of the conversion of a different functional group via rearrangement reaction
2.students should be familiar with
Types and principles of pericyclic reactions. What determines whether these pericyclic reactions go forwards or backward. Conservation of orbital symmetry and what conrotatory and disrotatory mean.Electrocyclic reactions and rules governing them, Cycloaddition reactions, and rules governing them.Sigmatropic reactions and rules governing them.
Course Learning Outcomes
1. On successful completion of this course, a student will be able to get the ability to demonstrate knowledge and understanding of essential facts, concepts, principles, and theories relating to retrosynthetic analysis and to apply such knowledge and understanding to the solution of problems related to the synthesis of organic target molecules
2.with respect to molecular orbital symmetry students recognizes the relative energies of bonding and antibonding molecular orbitals use of physical chemistry parameters in determining reaction mechanisms. Describe the key frontier orbital interactions that are involved in typical pericyclic, free radical, and nucleophilic addition substitution reactions.
Book Title : Organic synthesis The Disconnection Approach
Author : Stuart Warren, Paul Wyatt
Edition : 2nd edition,2008
Publisher : John Wiley and Sons, New York.
Book Title : Orbital symmetry and reaction mechanism
Author : HaleviEA
Edition : Ist edition,1992
Publisher : Springer Verlagee
Book Title : Pericyclic Reactions
Author : Giu GB and Willis MR
Edition : Ist edition
Publisher : Chapman and Hall,London