Principles of Organic Chemistry
I have started my teaching career once after the successful completion of my master's degree in 2009 from Sri Ramachandra University, Porur, Chennai. I have joined as an organic chemistry lecturer at Vikrama Simhapuri University, Nellore in 2009. I have been here for two years from 2009 to 2011, where I have taught organic chemistry, spectroscopy, biochemistry courses to UG, PG levels.
In 2018, I have taken Principles of Organic Chemistry classes in the Dept. of Chemical & Biological Engineering, Gachon University to the graduation students (Masters and Doctoral students). Basically, the coursework syllabus was designed for the graduate students to initiate the basic reactions and their mechanisms at the molecular level.
Later I joined as an Assistant Professor in Dept. of Chemistry, Eternal University, Himachal Pradesh, India where I have been there for 1 year from 2020 to 2021. Turing this tenure I had teaching experience at UG and PG levels.
Syllabus
The work has four chapters as follows
Chapter 1 - Fundamental Aspects in Organic Chemistry
Organic compounds with active functional groups, types of bonding, isomerism and its importance, types of reactions with mechanism, and determination of reaction mechanisms.
Chapter 2 - Amino acids and Protein Chemistry
Amino acids of proteins, general properties, peptide bonds, stability in pH, optical properties of amino acids, proteins, properties of proteins, applications of proteins in sensing, and catalysis.
Chapter 3 - Nucleic Acid Chemistry
Nitrogen bases, nucleosides, nucleotides, nitrogen base pairs, genes, structure and stability of DNA, RNA, structure of chromosome, and possible reactions with DNA and RNA for advanced research.
Chapter 4- Analytical tools
Types of analytical tools like UV-vis, FTIR (Fourier-transform infrared spectroscopy), NMR (Nuclear magnetic resonance spectroscopy), EPR (Electron paramagnetic resonance) and PL (Photoluminescence spectroscopy) for the analysis and determination of structure of molecules.
This is one of my sweet memory with beloved students. The picture was taken in front of Gachon University main building on December 21st, 2018 at 4:00 PM after successful completion of the final exam. In my class, I have students from Korea, India, Vietnam, and Ethiopia and all students are having excellent theoretical and experimental knowledge. Every class after, we had a significant interaction with all of them regarding current research and how can we apply the knowledge of basic chemistry into the original research.
Organic Chemistry
Theory
Unit-I
Stereochemical Principles, conformation, steric and stereoelectronic effects, enantiomeric and diastereomeric relationships, dynamic stereochemistry, prochiral relationships, conformations of acyclic molecules, cyclohexane derivatives, rings other than six-membered. Conformational effects on reactivity, angle strain an its effects on reactivity. Relationship between ring size and facility of ring closure. Torsional strain and related stereoelectronic effects.
Unit-II
Free radical reactions: generation, and characterization, characteristic of reaction mechanisms involving and electron transfer reactions. Carbanions and other nucleophilic carbon species and their reactions: Acidity of hydrocarbons carbanions, stabilized by functionalized groups, generation of carbon nucleophiles by deprotonations, regioselectivity, stereoselectivity, in enolate formation, other methods for enolate generation.
Unit-III
Alkylation of aldehydes, esters, nitriles, Michael addition, Aldol conversations, Robinson annulations, Amine catalyzed conversations, Mannich reactions acylation of carbanions, Wittig and related reaction, sulfur ylides, Darzen condensation, Stevens, Favorskii rearrangements, Stork-enamine reaction, Sharpless asymmetric epoxidations.
Unit-IV
Photochemistry: general principles about light absorption, electronic transitions, Jablonski diagram, intersystem crossing singlet and triplet states, Quantum yield. A brief introduction, and description of photochemical reactions of simple carbonyl compounds, alkenes, and aromatic compounds, Barton reaction, Hofmann-Loffler-Freytag reaction.
Unit-V
Concerted reactions, unimolecular rearrangement, and elimination: Electrocyclic, sigmatropic, and cycloadditions reactions, correlation diagrams and FMO theory. Diels-Alder reactions, general feature, dienophiles, dienes, (2+2) cycloadditions, Cope and Claisen arrangement, Ene reaction.
Practicals
1. Preparation of triphenylmethyl bromide from, triphenylmethane ( free radical bromination by use of NBS).
2. Preparation of 1,5-Diphenyl-1,4-pentadiene-3-one from benzaldehyde and acetone (Cross Aldol condensation).
3. Preparation of E/Z-α-phenylcinnamic acid from benzaldehyde and phenylacetic acid (Perkin reaction).
4. Preparation of 1,3,5-tribromobenzene from aniline (digitization, aromatic electrophilic substitution, and destination).
5. Preparation of 2,5-dihydroxy acetophenone from hydroquinone (Frie reaction).
6. Preparation of 3,5- diethoxycarbonyl-2,4-dimethyl pyrrole from ethyl acetoacetate (Knorr synthesis).
Organic Spectroscopy
Theory
Unit-I
IR: Spectroscopy: Characteristic vibration frequencies of various functional groups. A detailed study of vibrational frequencies of carbonyl compounds, ketone, aldehydes, esters, amides, anhydrides, lactose lactams, and conjugated carbonyl compounds. Factor affecting group frequencies, overtones, combination bands, and Fermi-resonance. FTIR and sampling technique. Structural information from vibrational spectra: Grou frequencies, characteristic band stretching frequencies.
Unit-II
UV-vis spectroscopy: Fieser-Woodward rules for conjugated dienes and carbonyl compounds, Fieser-Kunh rules for polyenes. UV spectra of aromatic compounds, and heteroaromatic compounds. calculation of λmax for the benzene derivatives.
Unit-III
1H NMR: General introduction and definitions, chemical shift, spin-spin interaction, shielding mechanism of measurement of chemical shift values and correlation for protons bonded to carbon and other nuclei. factor affecting chemical shift. Deuterium exchange, spin-spin coupling, factors affecting coupling constant. Simplification of complex spectra, nuclear magnetic double resonance, contact shift reagents, solvent effects, Nuclear-Over-Hauser effect (NOE). 13C NMR: Resolution and multiplicity, of 13C NMR, 1H-decoupling, noise decoupling, broadband decoupling, NOE signal enhancement, off-resonance, proton decoupling, applications of CMR.
Unit-IV
Theory, instrumentation, and modifications, unit mass and molecular ions, important terms- singly and doubly charged ions, metastable peak, base peak, isotropic mass peaks, relative intensity, FTMS etc., Recognition of M+ ion peak, general fragmentation rules. McLafferty rearrangement, structure elucidation of organic compounds, problems using the above spectroscopic techniques.
Disconnection Approach in Organic Synthesis
Theory
Unit-I
General introduction to organic synthesis, importance, and types of organic synthesis, linear and convenient synthesis, disconnection approach-Retrosynthetic analysis, the basic concepts and order of events. One group disconnections, synthetic equivalents to common synthons, functional group interconnections (FGI), target molecules, with two functional groups.
Unit-II
Reversal of Polarity (umpolung), amine synthesis, chemoselectivity, regioselectivity, stereoselectivity. Protection and deprotection of common functional groups like amines, alcohols, carbonyl groups in aldehydes, ketones and their derivatives.
Unit-III
Grignard reagents, organolithium, and zinc compounds for the organic synthesis, use of stabilized carbanions and related nucleophiles oxidation of alcohols to aldehydes and ketones.
Unit-IV
Nonstandard ylides, enolates, ynolate anion synthesis, and reactions. Dieckmann, Michael, Michael-Robinson, and Simmon-smith reactions, rearrangement reactions like Beckmann, Wagner-Meerwein, pinacol, Hofmann, Curtis, and Schmidt.
Computational Chemistry Lab
Theory
Use of Computer-Chem Draw, Chem Sketch, ISI-Draw, Chem Office 2011: Draw the structure of simple aliphatic, aromatic, heterocyclic compounds with different substituents.
Get the correct IUPAC name and predict the 1H and 13C NMR spectra.
Use of MS-Word, PowerPoint, Excell, and Origin Softwares for treatment of experimental data, X-Y plot, plotting graph, statistical analysis in chemistry.
Use of internet for literature survey.
Basic knowledge about Scifinder, Scopus and other search engines.
Structure elucidation using software for mass spectra analysis.
Organic Chemistry-II
Unit-I
Arenes and Aromaticity:
Nomenclature of benzene derivatives. The aryl group: Aromatic nucleus and side
chain. Structure of benzene: molecular formula and Kekule structure. Stability
and carbon-carbon bond lengths of benzene, resonance structure, MO picture.
Aromatic electrophilic substitution: general pattern of the mechanism, role of
σ-and π- complexes. Mechanism of nitration, halogenation, sulphonation, mercuration
and Friedel-Crafts reaction. Energy profile diagrams. Activating and
deactivating substituents, orientation andortho/pararatio.Side chain reactions
of benzenederivatives.Birchreduction.Methods of formation and chemical
reactions of alkylbenzenes and biphenyl.
Unit-II
Alkyl and Aryl Halides:
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.
Polyhalogencompounds: chloroform, carbon tetrachloride. 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 reactivity of alkyl halides vs. allyl, vinyl and aryl
halides.Synthesis and uses of DDT and BHC.
Uni-III
Alcohols: Classification
and nomenclature of Monohydric alcohols - nomenclature, methods of formation by
reduction of aldehydes, ketones, carboxylic acids and esters. Hydrogen
bonding.Acidicnature.Reactions of alcohols. Dihydric alcohols - nomenclature,
methods of formation, chemical reactions of vicinal glycols, oxidative cleavage
[Pb(OAc)4 and HIO4 and pinacol-pinacolone rearrangement].
Trihydric alcohols - nomenclature and methods of formation, chemical reactions
of glycerol.
Unit-IV
Phenols:Nomenclature,
structure and bonding. Preparation of phenols, physical properties and acidic
character.Comparative acidic strengths of alcohols and phenols, resonance
stabilization of phenoxideion.Reactions of phenols - electrophilic aromatic
substitution, Acylation and carboxylation.Mechanisms of Fries rearrangement,
Claisen rearrangement, Gatterman synthesis, Hauben-Hoesch reaction,
Ledrer-Manasse reaction and Reimer-Tiemann reaction.
Unit-V
Ethers and Epoxides:
Nomenclature of ethers and methods of their formation, physical properties.
Chemical reactions - cleavage and auto-oxidation, Ziesel'smethod.Synthesis of
epoxides. Acid and base-catalyzed ring opening of epoxides, orientation of epoxide
ring opening, reactions of Grignard and organolithium reagents with epoxides.
Practicals
Preparation of Organic Compounds:
Preparation of (i) iodoform
(ii) Benzamide
(iii) acetanilide
(iv) nitrobenzene
(v) m-dinitrobenzene
Natural Products Chemistry
Unit-I
Terpenoids
and Carotenoids: Classification, general methods of structure determination.
Synthesis of citral, geraniol, a
-terpineol, menthol, longifolene and a-carotene.
Synthesis of Quercetin, myrcetin, cyanidin Chloride, hirsutidin Chloride.
Unt-II
Steroids,
basic skeleton, stereochemistry, structure determination of cholesterol by
degradation experiments, synthesis cholesterol, testosterone, progesterone, cortisone.
Unit-III
Alkaloids: General method structure elucidation, classification based on nitrogen heterocyclic ring structure, Synthesis of quinine, morphine, chloroquine and primaquine.
Unit-IV
Vitamins:
Synthesis of Vitamin A, E and K. Sulpha drugs, Antibiotics: penicillin G, V,
Chloramphenicol, cephalosporin, tetracycline and Prostaglandins: Synthesis of
PGE2 and PGF22.