JAWAHARLAL NEHRU TECHNOLOGICAL UNIVERSITY HYDERABAD

Overview

Scope: This subject deals with classification and nomenclature of simple organiccompounds, structural isomerism, intermediates forming in reactions, important physical properties, reactions and methods of preparation of these compounds. The syllabus also emphasizes on mechanisms and orientation of reactions.

Course Objectives

Upon completion of the course the student shall be able to

• write the structure, name and the type of isomerism of the organic compound
• write the reaction, name the reaction and orientation of reactions
• account for reactivity/stability of compounds,
• identify/confirm the identification of organic compound General methods of preparation and reactions of compounds superscripted with asterisk (*) to be explained To emphasize on definition, types, classification, principles/mechanisms, applications, examples and differences

UNIT - I

Classification, nomenclature and isomerism Brief review of structural theory of organic chemistry, hybridization, bond length, bond angle, bond energy; inductive effect, electromeric effect, resonance, hyperconjugationand their application in the analysis of strength of organic acids, bases and stability of organic compounds; structure, shape and reactivity of nucleophiles, electrophiles and free radicals; cleavage of bonds-homolysis and heterolysis Classification of Organic Compounds: Common and IUPAC systems of nomenclature of organic compounds (up to 10 Carbons open chain and carbocyclic compounds) Structural isomerisms in organic compounds Types of organic reactions: Addition reactions-electrophilic, nucleophilic and free radical; Substitution reactions-electrophilic, nucleophilic and free radical; elimination and rearrangement reactions

UNIT - II

Alkanes*, Alkenes* and Conjugated dienes* Functional group approach for the following reactions (preparations & reactions) to be studied in context to their structure Alkanes: Preparation: Catalytic hydrogenation, Wurtz reaction, Kolbe’s synthesis, from Grignard reagent. Reactions: Free radical Substitution: Halogenation, Synthesis of cycloalkanes and different kinds of strains in cycloalkanes Alkenes: Preparation: Elimination reactions: Dehydration of alkenes and dehydrohalogenation of alkyl halides (Saytzeff’s rule); cis alkenes (Partial catalytic hydrogenation) and trans alkenes (Birch reduction). Reactions: cis-addition (alk. KMnO4) and trans-addition (bromine), Addition of HX (Markownikoff’s and anti- Markownikoff’s addition), Hydration, Ozonolysis, oxymecuration-demercuration, Hydroboration-oxidation, stability of alkenes Conjugated dienes: Stability, Diel-Alder, electrophilic addition, free radical additionreactions of conjugated dienes, allylic rearrangement Alkynes: Preparation: Acetylene from CaC2 and conversion into higher alkynes; by dehalogenation of tetra halides and dehydrohalogenation of vicinal-dihalides. Reactions: formation of metal acetylides, addition of bromine and alkaline KMnO4, ozonolysis and oxidation with hot alk. KMnO4

UNIT - III

Alkyl halides* SN1 and SN2 reactions - kinetics, order of reactivity of alkyl halides, stereochemistry andrearrangement of carbocations, SN1 versus SN2 reactions, Factors affecting SN1 and SN2 reactions, Preparation: from alkenes and alcohols. Reactions: hydrolysis, nitrite & nitro formation, nitrile & isonitrile formation.

Alcohols: Preparation ofalcohols: using Grignard reagent, Ester hydrolysis, Reduction of aldehydes, ketones, carboxylic acid and esters. Reactions: With sodium, HX (Lucas test), esterification, oxidation reactions.

UNIT - IV

Carbonyl compounds* (Aldehydes and ketones) Preparation: from acid chlorides and from nitriles. Reactions: Reaction with HCN, ROH, NaHSO3, NH2-G derivatives. Aldol Condensation, Cannizzaro’s reaction, Wittig reaction, Benzoin condensation, Clemensen reduction and Wolff Kishner reduction, Meerwein-Pondorff Verley reduction, Analysis of aldehydes and ketones: haloform test, 2,4-DNP test, Tollens and Fehling test.

UNIT - V

Carboxylic acids*(aliphatic and aromatic) Preparation and reactions of carboxylic acids. Carboxylic acid derivatives (aliphatic): Preparation: Acid chlorides, Anhydrides, Esters and Amides from acids and their interconversion. Acidity of carboxylic acids, effect of substituents on acidity, inductive effect and qualitative tests for carboxylic acids, amide and ester Aliphatic amines* - Preparation: from alkyl halides, Gabriel’s Phthalimide synthesis, Hofmann Bromamide reaction. Reactions: Hofmann vs. Saytzeff elimination, Quaternary ammonium salts, Carbylamine test. Basicity, effect of substituent on Basicity. Qualitative tests.

TEXT BOOKS

(Latest Editions)

• 1. Organic Chemistry by Morrison and Boyd
• 2. Organic Chemistry by I.L. Finar, Volume-I
• 3. Algarsamy V., Pharmaceutical organic Chemistry, Pharma Med Press
• 4. Textbook of Organic Chemistry by B.S. Bahl&ArunBahl.
• 5. Organic Chemistry by P.L. Soni
• 6. Practical Organic Chemistry by Mann and Saunders.
• 7. Vogel’s text book of Practical Organic Chemistry
• 8. Advanced Practical organic chemistry by N.K. Vishnoi.
• 9. Introduction to Organic Laboratory techniques by Pavia, Lampman and Kriz.
• 10. Pharmaceutical organic Chemistry-1, Pooja Chawla.
• 11. McMurry E. John, Organic Chemistry, Cengage