COURSE SUMMARY
Course Title: 
Functional Groups, Heterocyclic Compounds and Natural Products
Course Code: 
18CHY311
Year Taught: 
2018
Semester: 
6
Degree: 
Undergraduate (UG)
School: 
School of Arts and Sciences
Campus: 
Mysuru

'Functional Groups, Heterocyclic Compounds and Natural Products' is a course offered at the School of Arts and Sciences, Amrita Vishwa Vidyapeetham, Mysuru campus.

To develop an understanding of Natural Products,Alcohols and Phenols, Carbonyl Compounds, Organic Compounds of Nitrogen and Heterocyclic Compounds.

Unit I: Alcohols and Phenols
Monohydric alcohols: Nomenclature, methods of formation (reduction of aldehydes, ketones, carboxylic acids and esters). Hydrogen bonding, Acidic nature.Reactions of alcohols (oxidation, esterification, dehydration). Dihydric alcohols: Nomenclature, methods of formation (from alkenes and alkyl dihalides), chemical reactions of vicinal glycols - oxidative cleavage [Pb(OAc)4 and HIO4] and Pinacol-pinacolone rearrangement. Trihydric alcohols: Nomenclature and methods of formation (from alkenes and alkenals), chemical reactions of glycerol (with nitric acid, oxalic acid and HI). Phenols: Nomenclature, structure and bonding, Preparation of phenol, resorcinol and 1 and 2- naphthols (one method each). Physical properties and acidic character of phenol.Comparative acidic strengths of alcohols and phenols, resonance stabilization of phenoxide ion. Reactions of phenols: Electrophilic aromatic substitution, acylation and carboxylation. Mechanisms of Fries rearrangement, Claisen rearrangement, Gatterman synthesis, Houben-Hoesch reaction, LedererManasse reaction and Reimer-Tiemann reaction.

Unit II: Carbonyl Compounds
Aldehydes and Ketones: Synthesis of aldehydes and ketones with particular reference to the synthesis of aldehydes from acid chlorides, synthesis of aldehydes and ketones using 1,3-dithianes, synthesis of ketones from nitriles and from carboxylic acids. Physical properties.Benzoin, aldol, Perkin and Knoevenagel condensations.Use of acetals as protecting group.Baeyer-Villager oxidation of ketones, Cannizzaro reaction.MPV, Clemmensen, Wolff-Kishner, LiAlH4 and NaBH4 reductions.Halogenation of enolizable ketones. An introduction to α, β-unsaturated aldehydes and ketones. Carboxylic Acids and their Derivatives: Reactions of carboxylic acids: HVZ reaction, synthesis of acid chlorides, esters and amides. Reduction of carboxylic acids.Mechanism of decarboxylation.Methods of formation and chemical reactions hydroxy acids – malic, tartaric and citric acids. Unsaturated monocarboxylic acids: Methods of formation and chemical reactions Dicarboxylic acids: Methods of formation and effect of heat and dehydrating agents. Carboxylic acid derivatives: Structure and nomenclature of acid chlorides, esters, amides and acid anhydrides. Preparation of carboxylic acid derivatives, chemical reactions. Mechanism of esterification and hydrolysis (acid, base conditions).

Unit III: Organic Compounds of Nitrogen
Nitro Compounds: Introduction, Preparation of nitroalkanes and nitroarenes. Chemical reactions of nitroalkanes.Mechanism of nucleophilic substitution in nitroarenes and their reductions in acidic, neutral and alkaline media.Picric acid. Aliphatic and Aromatic amines: Structure and nomenclature of amines, Preparation of alkyl and aryl amines (reduction of nitro compounds, nitrites), reductive amination of aldehydic and ketonic compounds. Gabriel-phthalimide reaction, Hofmann bromamide reaction.Reactivity, physical properties, stereochemistry of amines.Separation of a mixture of primary, secondary and tertiary amines (Hinsberg’s method).Structural features effecting basicity of amines. Amine salts as phase – transfer catalysts. Reactions of amines, electrophilic aromatic substitution in aryl amines, reactions of amines with nitrous acid. Synthetic transformations by aryl diazonium salts, azo coupling.

Unit IV: Heterocyclic Compounds
Introduction, methods of formation of five membered heterocycles – furan, thiophene and pyrrole.Molecular orbital picture and aromatic characteristics of pyrrole, furan, thiophene and their chemical reactions with particular emphasis on the mechanism of electrophilic substitution. Six membered heterocycles: methods of formation of pyridine, mechanism of nucleophilic substitution reactions in pyridine derivatives. Comparison of basicity of pyridine, piperidine and pyrrole. Introduction to condensed five and six-membered heterocycles, preparation and reactions of Indole, quinoline and isoquinoline with special reference to Fischer indole synthesis, Skraup synthesis and Bischler-Napieralski synthesis.Mechanism of electrophilic substitution reactions of indole, quinoline and isoquinoline.

Unit V: Natural Products
Carbohydrates: Introduction, classification and nomenclature. Configuration of monosaccharides.Erythro and threo diastereomers.Interconversions in carbohydrates – glucose to fructose, fructose to glucose, aldopentose to aldohexose and aldohexose to aldopentose.Epimerisation, mechanism of osazone formation, Formation of glycosides, ethers and esters.Determination of ring size of monosaccharides. Structural elucidation of D(+) glucose. Mechanism of Mutarotation.Constitution of disaccharides - maltose, sucrose and lactose.Introduction to polysaccharides (starch and cellulose) without involving structure determination. Alkaloids: Introduction, general methods of structural determination, structural elucidation of Conine, Nicotine and piperine Terpinoids : Introduction, isoprene rule, structural elucidation of Citral and Menthol. Amino acids, Peptides, Proteins and Nucleic acids Classification, structure and stereochemistry of amino acids.Acid-base behaviour, isoelectric point and electrophoresis. Preparation and reactions of α- amino acids. Classification of proteins.Peptide structure determination - end group analysis, selective hydrolysis of peptides.Solid-phase peptide synthesis.Primary and secondary structures of proteins.Protein denaturation. Nucleic acids: Introduction, constituents of nucleic acids. Ribonucleosides and Ribonucleotides.The double helical structure of DNA.

Textbooks:
  1. R. T. Morrison and R.N. Boyd, ‘Organic Chemistry’, 6th Edition - Prentice Hall of India.

References:
  1. M. K. Jain and S. C. Sharma 'Modern Organic Chemistry', 3rd Edition, Visal Publishing Company Co.
  2. K. S. Tewari and N. K. Vishnoi, 'Organic Chemistry', 3rd Edition, Vikas Publishing House.
  3. I.L. Finar, Organic Chemistry - Volume I & II - Pearson Education.