Heterocyclic Compounds and Stereochemistry

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Unit 1 · Carboxylic Acids, Amines and Polynuclear Aromatic Hydrocarbons 15 hrs

Aliphatic and aromatic carboxylic acids — preparation (oxidation of alcohols, carbonation of Grignard reagents, the Kolbe–Schmidt reaction), acidity and the effect of substituents, and reactions including nucleophilic acyl substitution, decarboxylation and the Hell–Volhard–Zelinsky reaction, with the pharmaceutical applications of benzoic, salicylic and acetylsalicylic acid; aliphatic and aromatic amines — preparation, basicity and characteristic reactions; and polynuclear aromatic hydrocarbons, their classification and synthesis including the Haworth synthesis.

Unit 2 · Alcohols and Phenols 7 hrs

Preparation of alcohols including oxymercuration–demercuration and the reduction of carbonyl compounds; the comparative acidity of phenols versus alcohols; the characteristic reactions of phenols including the Reimer–Tiemann reaction, halogenation and nitration; and the pharmaceutical applications of glycerine, thymol and paracetamol.

Unit 3 · Stereochemistry 6 hrs

Optical activity and chirality; enantiomerism, diastereoisomerism and meso compounds; elements of symmetry; optical isomerism in compounds with one and two chiral centres; and the R/S and D/L systems of nomenclature.

Unit 4 · Conformational Analysis and Geometrical Isomerism 10 hrs

Conformational isomerism in ethane, n-butane and cyclohexane, including axial and equatorial bonds and ring inversion; geometrical isomerism and cis–trans (E/Z) nomenclature; and the influence of stereochemistry on drug action.

Unit 5 · Heterocyclic Chemistry 7 hrs

The nomenclature and classification of heterocyclic systems; the aromaticity, synthesis and reactivity of five-membered rings — the electrophilic substitution reactions of pyrrole, furan and thiophene; six-membered rings including pyridine; fused systems such as indole, quinoline and isoquinoline; and their occurrence in medicinally important molecules.