| Course Name | Hydrocarbons, Alkyl and Aryl Halides |
| Course Code | 25CHY201 |
| Campus |
Practical component: (15 hours)1. Qualitative analysis of mono functional organic compounds through functional group analysis. Determination of physical constant. Preparation of suitable derivative.Acids AlcoholsAldehydesAmides Amines Halogenated hydrocarbons Hydrocarbons Ketones Nitro compounds Phenols
Fundamentals of organic reaction mechanism: Types of reagents Electrophiles and Nucleophiles. Substitution, Addition, Elimination and Rearrangement. Reactive intermediates with examples Carbocations, Carbanions and Free radicals. Electron displacement effects – Inductive, inductomeric, electromeric, mesomeric, resonance, hyper conjugation and steric effects. Aliphatic nucleophilic substitutions, mechanism of SN1,SN2- effects of structure substrate, solvent, nucleophile and leaving groups – Stereochemistry- Walden inversion Elimination Reactions:-Hoffmann and Saytzeff rules- cis and trans eliminations mechanisms of E1 and E2 reactions. Elimination versus substitution.Addition reactions- mechanisms of addition of Bromine and hydrogen halides to double bonds- Markownikoffs rule and peroxide effect. Polymerisation reactions-Types of polymerisation – free radical, cationic and anionic polymerisations including mechanism.
Stereochemistry of Organic Compounds : Optical Isomerism: Structural changes responsible for properties: elements of symmetry, molecular chirality, enantiomers, stereogeniccentre, optical activity, properties of enantiomers, chiral and achiral molecules with two stereogeniccentres, diastereomers, threo and erythrodiastereomers, meso compounds, resolution of enantiomers, inversion, retention and racemization and asymmetric synthesis. Relative and absolute configuration, sequence rules, D & L and R & S systems of nomenclature. Geometric isomerism: Determination of configuration of geometric isomers. Cis trans and E & Z system of nomenclature, geometric isomerism in oximes and alicyclic compounds. Conformational isomerism: Difference between configuration and conformation. Conformational analysis of ethane and n-butane; conformations of cyclohexane, axial and equatorial bonds, conformation of mono alkyl substituted cyclohexane derivatives. Review of Newman projection and Sawhorse formulae, Fischer and flying wedge formulae.
Aliphatic Hydrocarbons – Alkanes: Methods of formation (with special reference to Wurtz reaction, Kolbe reaction, Corey-House reaction and decarboxylation), physical properties and chemical reactions of alkanes (halogenation, nitration, sulphonation, oxidation and isomerisation reactions) Mechanism of free radical halogenation of alkanes: orientation, reactivity and selectivity. Cycloalkanes: methods of formation (from acetoacetic ester / malonic ester and Dieckmann reaction), chemical reactions (halogenation), Baeyers strain theory and its limitations. Ring strain in small rings (cyclopropane and cyclobutane), theory of strainless rings. Alkenes: Accounting for Reactions due to unsaturation in compounds. Regioselectivity in alcohol dehydration. Hofmann elimination, physical properties and relative stabilities of alkenes. Chemical reactions of alkenes mechanism of hydrogenation, electrophilic and free radical additions, Markownikoffs rule, hydroboration followed by oxidation, oxymercuration reduction. Epoxidation, ozonolysis, hydration, hydroxylation and oxidation with KMnO4. Substitution at the allylic and vinylic positions of alkenes. Cycloalkenes: Methods of formation and chemical reactions of cycloalkenes. Alkadienes: Isolated, conjugated and cumulated dienes. Structure of allenes and butadiene, methods of formation, polymerization. Chemical reactions 1,2 and 1,4 additions. Diels-Alder reaction. Alkynes: Methods of formation (alkylation of acetylene and by elimination reactions). Acidity of alkynes. Chemical reactions of alkynes: Mechanism of electrophilic and nucleophilic addition reactions, hydroboration oxidation, metal-ammonia reductions, oxidation
Aromatic Hydrocarbons: Structure of benzene: molecular formula and Kekule structure. Stability and carbon-carbon bond lengths of benzene, resonance structure, MO picture. Aromaticity: The Huckel rule, aromatic ions. Aromatic electrophilic substitution: General pattern of the mechanism, role of – and – complexes. Mechanism of nitration, halogenation, sulphonation, mercuration and Friedel-Crafts reaction. Energy profile diagrams. Activating and deactivating substituents, orientation and ortho/ para ratio. Side chain reactions of benzene derivatives. Birch reduction. Methods of formation and chemical reactions of alkylbenzenes, alkynylbenzenes and biphenyl.
Alkyl and Aryl Halides:A study of Alkyl halides highlighting its synthetic applications. Nomenclature and classes of alkyl halides, methods of formation, chemical reactions. Mechanisms of nucleophilic substitution reactions of alkyl halides SN2 and SN1 reactions with energy profile diagrams. Polyhalogen compounds:chloroform, carbon tetrachloride. Aryl halides: Methods of formation of aryl halides, nuclear and side chain reactions. The addition- elimination and the elimination-addition mechanisms of nucleophilic aromatic substitution reactions. Relative reactivities of alkyl halides vsallyl, vinyl and aryl halides. Synthesis and uses of DDT and BHC
OBJECTIVES: To enable students to develop an understanding of chemistry of hydrocarbons and their halogenated derivatives.
Course Outcome:
|
CO1 |
Explain the mechanism of organic reactions and to predict the products formed in a reaction. |
|
CO2 |
Recognize and assign stereo chemical designations of organic compounds. |
|
CO3 |
Describe the formation, physical and chemical properties of aliphatic hydrocarbons. |
|
CO4 |
Apply the concept of aromaticity to explain the structure, stability and properties of aromatic hydrocarbons. |
|
CO5 |
Describe chemical reactions involving alkyl and aryl halides and their synthetic applications. |
|
CO6 |
Apply qualitative methods for identification of mono functional organic compounds. |
CO – PO mapping
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PO1 |
PO2 |
PO3 |
PO4 |
PO5 |
PO6 |
PO7 |
PO8 |
PO9 |
PO10 |
PSO1 |
PSO2 |
PSO3 |
PSO4 |
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CO1 |
3 |
– |
– |
– |
– |
– |
– |
– |
– |
– |
2 |
– |
– |
3 |
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CO2 |
3 |
– |
– |
– |
– |
– |
– |
– |
– |
– |
2 |
– |
– |
3 |
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CO3 |
3 |
– |
– |
– |
– |
– |
– |
– |
– |
– |
2 |
– |
– |
3 |
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CO4 |
3 |
– |
– |
– |
– |
– |
– |
– |
– |
– |
2 |
– |
– |
3 |
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CO5 |
3 |
– |
– |
– |
– |
– |
– |
– |
– |
– |
2 |
– |
– |
3 |
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CO6 |
2 |
– |
3 |
– |
– |
– |
– |
– |
– |
– |
2 |
– |
– |
3 |
TEXTBOOKS:1) R. T. Morrison and R. N. Boyd, Organic Chemistry, 6thEdition (1994) – Prentice Hall of India2) M. K. Jain and S. C. Sharma Modern Organic Chemistry 3rdEdition (2003), Vishal Publishing Company Co.REFERENCES:1) K. S. Tewari; N. K. Vishnoi; S. N. Mehrotra, A Text Book of Organic Chemistry, 2nd Edition (2003), Vikas Publishing Pvt. Ltd.2) S. C. Pal, Nomenclature of Organic Compounds (2016), Narosa Publishing Company3) Peter Sykes, A Guide book to Mechanism in Organic Chemistry: 6thEdition (2003), Pearson Education. 4) P. S. Kalsi, Organic Reactions and their Mechanisms New Age International Publishers, (2004). 5) I. L. Finar, Organic Chemistry, 6thEdition (1982). Vol-I, Pearson Education.
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