SEMESTER III
CH3CRT03 - ORGANIC CHEMISTRY – I
Credits – 3 (54 Hrs)
(Reaction mechanisms expected only wherever mentioned)
Unit 1: Fundamentals of Organic Chemistry (8 Hrs)
Classification and IUPAC system of nomenclature of common organic compounds (both aliphatic and aromatic). Line diagram drawing. Factors affecting reaction mechanism. Polarity of bonds. Electronic displacements: Inductive effect, electromeric effect, mesomeric effect, resonance and hyperconjugation. steric effects. Cleavage of bonds: Homolysis and heterolysis with suitable examples. curly arrow rules,formal charges. Types of reagents: Nucleophiles and electrophiles.
Reactive intermediates: Carbocations, carbanions, free radicals and carbenes – types, shape and relative stability. Types of organic reactions: Addition, elimination, substitution, rearrangement and redox reactions (definition and one example each).
Unit 2: Stereochemistry (15 Hrs) Stereoisomerism – definition, classification.
Optical isomerism: Optical activity, specific rotation, concept of chirality (upto two carbon atoms). Configuration. Enantiomerism, diastereomerism and meso compounds. Racemic mixture and methods of resolution. Asymmetric synthesis (partial and absolute). Threo and erythro; d and l designations; Cahn-Ingold-Prelog rules: R/ S notation (for upto 2 chiral carbon atoms).
Geometrical isomerism: cis–trans, syn-anti and E/Z nomenclature (for upto two C=C systems) with C.I.P rules. Methods of distinguishing geometrical isomers.
Conformational analysis: Conformational analysis with respect to ethane, butane and
cyclohexane. Relative stability and energy diagrams. Inter conversion of Wedge formula, Newman, Sawhorse and Fischer projection formulae. Chair, boat and twist boat forms of cyclohexane with energy diagrams. Conformation of methyl cyclohexane. Origin of ring strain in cyclic systems. Baeyer’s strain theory.
Unit 3: Aliphatic Hydrocarbons and Alkyl Halides (12 Hrs)
Alkanes: Preparation - catalytic hydrogenation, Wurtz reaction, Wurtz-Fittig reaction, from Grignard reagent. Reactions - free radical substitution - halogenation.
Alkenes: Preparation - Elimination reactions - mechanism of E1 and E2 reactions. Dehydration of alkenes and dehydrohalogenation of alkyl halides (Saytzeff’s and Hofmann’s rules). Reactions - cis-addition (alkaline KMnO4) and trans-addition (bromine). Addition of HX (Markownikoff’s and anti-Markownikoff’s addition with mechanisms), Hydration, Ozonolysis. N N Alkynes: Preparation - Acetylene from CaC2 and conversion into higher alkynes; by dehalogenation of tetra halides and dehydrohalogenation of vicinal dihalides. Reactions - Acidity of alkynes, formation of metal acetylides, alkylation of terminal alkynes and conversion into higher alkynes, addition of bromine and alkaline KMnO4. Alkyl Halides: Preparation - From alkenes and alcohols. Reactions - Types of aliphatic nucleophilic substitution reactions - S 1
and S 2 mechanisms with stereochemical aspects and effects of substrate structure, solvent, nucleophile and leaving group. Organometallic compounds of Mg (Grignard reagents) – Formation, structure and important
reactions/synthetic applications.
Unit 4: Aromatic Hydrocarbons and Aryl Halides (15 Hrs)
Aromaticity : Definition, Hückel’s rule - application to benzenoid (benzene, naphthalene and anthracene) and non-benzenoid (cyclopropenyl cation, cyclopentadienyl anion and tropylium cation) compounds.
Benzene: Molecular orbital picture and resonance energy. Preparation - from phenol, by decarboxylation, from acetylene, from aromatic acids. Reactions - Electrophilic aromatic substitution: nitration, halogenation, sulphonation and Friedel-Craft’s reaction (alkylation and acylation) with their mechanism. Orientation of aromatic substitution. ortho, para and meta
directing effects of groups. Ring activating and deactivating groups with examples.
Naphthalene and Anthracene: Molecular orbital picture and resonance energy. Preparation - (of Naphthalene): Haworth synthesis
Reactions - Electrophilic substitutions (halogenation, nitration and sulphonation) of
naphthalene.
Aryl Halides: Preparation - chloro, bromo and iodo-benzene from phenol, Sandmeyer and
Gattermann reactions. Reactions - aromatic nucleophilic substitutions – bimolecular
displacement mechanism, elimination-addition (benzyne intermediate) mechanism.
Unit 5: Pericyclic Reactions (4 Hrs)
Classification – electrocyclic reactions, cycloadditions - Diels-Alder reaction and Sigmatropic
rearrangements - Claisen rearrangement (with mechanism).
References
1. Morrison, R.T., Boyd, R.N. & Bhattacharjee, S.K. Organic Chemistry, 7th
ed.,
Dorling Kindersley (India) Pvt. Ltd (Pearson Education), 2011.
2. Graham Solomon, T.W., Fryhle, C.B. & Snyder, S.A. Organic Chemistry, John
Wiley & Sons, 2014.
3. McMurry, J. Organic Chemistry, 7th ed. Cengage Learning, 2013.
4. Sykes, P. A Guidebook to Mechanism in Organic Chemistry, Orient Longman, 1988.
5. Eliel, E.L. & Wilen, S.H. Stereochemistry of Organic Compounds, Wiley, 1994.
6. Finar, I.L. Organic Chemistry (Vol. 1 & 2), Dorling Kindersley (India) Pvt. Ltd
(Pearson Education).
7. Jain, M.K. & Sharma, S.C. Modern Organic Chemistry, Vishal Publishing Co. 2010.
8. Bahl, A. & Bahl, B.S. Advanced Organic Chemistry, S. Chand, 2010.
CH3CRT03 - ORGANIC CHEMISTRY – I
Credits – 3 (54 Hrs)
(Reaction mechanisms expected only wherever mentioned)
Unit 1: Fundamentals of Organic Chemistry (8 Hrs)
Classification and IUPAC system of nomenclature of common organic compounds (both aliphatic and aromatic). Line diagram drawing. Factors affecting reaction mechanism. Polarity of bonds. Electronic displacements: Inductive effect, electromeric effect, mesomeric effect, resonance and hyperconjugation. steric effects. Cleavage of bonds: Homolysis and heterolysis with suitable examples. curly arrow rules,formal charges. Types of reagents: Nucleophiles and electrophiles.
Reactive intermediates: Carbocations, carbanions, free radicals and carbenes – types, shape and relative stability. Types of organic reactions: Addition, elimination, substitution, rearrangement and redox reactions (definition and one example each).
Unit 2: Stereochemistry (15 Hrs) Stereoisomerism – definition, classification.
Optical isomerism: Optical activity, specific rotation, concept of chirality (upto two carbon atoms). Configuration. Enantiomerism, diastereomerism and meso compounds. Racemic mixture and methods of resolution. Asymmetric synthesis (partial and absolute). Threo and erythro; d and l designations; Cahn-Ingold-Prelog rules: R/ S notation (for upto 2 chiral carbon atoms).
Geometrical isomerism: cis–trans, syn-anti and E/Z nomenclature (for upto two C=C systems) with C.I.P rules. Methods of distinguishing geometrical isomers.
Conformational analysis: Conformational analysis with respect to ethane, butane and
cyclohexane. Relative stability and energy diagrams. Inter conversion of Wedge formula, Newman, Sawhorse and Fischer projection formulae. Chair, boat and twist boat forms of cyclohexane with energy diagrams. Conformation of methyl cyclohexane. Origin of ring strain in cyclic systems. Baeyer’s strain theory.
Unit 3: Aliphatic Hydrocarbons and Alkyl Halides (12 Hrs)
Alkanes: Preparation - catalytic hydrogenation, Wurtz reaction, Wurtz-Fittig reaction, from Grignard reagent. Reactions - free radical substitution - halogenation.
Alkenes: Preparation - Elimination reactions - mechanism of E1 and E2 reactions. Dehydration of alkenes and dehydrohalogenation of alkyl halides (Saytzeff’s and Hofmann’s rules). Reactions - cis-addition (alkaline KMnO4) and trans-addition (bromine). Addition of HX (Markownikoff’s and anti-Markownikoff’s addition with mechanisms), Hydration, Ozonolysis. N N Alkynes: Preparation - Acetylene from CaC2 and conversion into higher alkynes; by dehalogenation of tetra halides and dehydrohalogenation of vicinal dihalides. Reactions - Acidity of alkynes, formation of metal acetylides, alkylation of terminal alkynes and conversion into higher alkynes, addition of bromine and alkaline KMnO4. Alkyl Halides: Preparation - From alkenes and alcohols. Reactions - Types of aliphatic nucleophilic substitution reactions - S 1
and S 2 mechanisms with stereochemical aspects and effects of substrate structure, solvent, nucleophile and leaving group. Organometallic compounds of Mg (Grignard reagents) – Formation, structure and important
reactions/synthetic applications.
Unit 4: Aromatic Hydrocarbons and Aryl Halides (15 Hrs)
Aromaticity : Definition, Hückel’s rule - application to benzenoid (benzene, naphthalene and anthracene) and non-benzenoid (cyclopropenyl cation, cyclopentadienyl anion and tropylium cation) compounds.
Benzene: Molecular orbital picture and resonance energy. Preparation - from phenol, by decarboxylation, from acetylene, from aromatic acids. Reactions - Electrophilic aromatic substitution: nitration, halogenation, sulphonation and Friedel-Craft’s reaction (alkylation and acylation) with their mechanism. Orientation of aromatic substitution. ortho, para and meta
directing effects of groups. Ring activating and deactivating groups with examples.
Naphthalene and Anthracene: Molecular orbital picture and resonance energy. Preparation - (of Naphthalene): Haworth synthesis
Reactions - Electrophilic substitutions (halogenation, nitration and sulphonation) of
naphthalene.
Aryl Halides: Preparation - chloro, bromo and iodo-benzene from phenol, Sandmeyer and
Gattermann reactions. Reactions - aromatic nucleophilic substitutions – bimolecular
displacement mechanism, elimination-addition (benzyne intermediate) mechanism.
Unit 5: Pericyclic Reactions (4 Hrs)
Classification – electrocyclic reactions, cycloadditions - Diels-Alder reaction and Sigmatropic
rearrangements - Claisen rearrangement (with mechanism).
References
1. Morrison, R.T., Boyd, R.N. & Bhattacharjee, S.K. Organic Chemistry, 7th
ed.,
Dorling Kindersley (India) Pvt. Ltd (Pearson Education), 2011.
2. Graham Solomon, T.W., Fryhle, C.B. & Snyder, S.A. Organic Chemistry, John
Wiley & Sons, 2014.
3. McMurry, J. Organic Chemistry, 7th ed. Cengage Learning, 2013.
4. Sykes, P. A Guidebook to Mechanism in Organic Chemistry, Orient Longman, 1988.
5. Eliel, E.L. & Wilen, S.H. Stereochemistry of Organic Compounds, Wiley, 1994.
6. Finar, I.L. Organic Chemistry (Vol. 1 & 2), Dorling Kindersley (India) Pvt. Ltd
(Pearson Education).
7. Jain, M.K. & Sharma, S.C. Modern Organic Chemistry, Vishal Publishing Co. 2010.
8. Bahl, A. & Bahl, B.S. Advanced Organic Chemistry, S. Chand, 2010.
- Teacher: Ms. Bijimol D
- Teacher: Dr Soby Daniel
- Teacher: Dr Laigi Joseph
Course Outcomes:
1. To familiarize the chemical processes used in industry
1. To familiarize the chemical processes used in industry
- Teacher: Ms. Bijimol D
- Teacher: Dr Soby Daniel
- Teacher: Lintamary Jose