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Course Detail

Course Name Physical Methods in Organic Chemistry
Course Code 26CHY513
Program M.Sc. Organic Chemistry
Semester 2
Credits 4
Campus Mysuru

Syllabus

Unit 1

Electronic Spectroscopy (10 hours)

Principle of UV spectroscopy, Types of electronic transitions in molecules, selection rules, Concept of chromophore, Solvent effect, Fluorescence and phosphorescence, Characteristic absorption of organic compounds, Woodward-Fieser rules and Fieser-Kuhn rules and their applications, Substituent effects, Ring size and strain on spectral characteristics, Stereochemical effect and non-conjugated interactions, Model compound studies.

Unit 2

Vibrational Spectroscopy (12 hours)

Introduction to IR spectroscopy, Selection rules, normal modes, vibration-rotation spectra, IR spectra of organic, characteristics frequencies of functional groups, Effects of Inductive & Mesomeric Effects, ring strain, hydrogen bonding (inter and intra) and stereochemical effects on absorption, effects of phase, temperature and solvent o n IR spectra.

Introduction to Microwave spectroscopy:  Rotational energy levels, selection rules, classification of molecules based on Moment of Inertia, application of microwave spectroscopy.

Introduction to Raman spectroscopy: Rotational Raman and Vibrational Raman Spectra, Stokes and anti – Stokes lines, Complementary nature of IR and Raman spectra. Applications of Raman spectroscopy.

Unit 3

Spin Resonance Spectroscopy (12 hours)

Nuclear Magnetic Resonance – Working principles of NMR, Instrumentation, chemical shift, factors affecting chemical shifts, shielding and deshielding effects, signal integration, spin-spin coupling: vicinal, geminal and long range, coupling constants and factors affecting coupling constant. Applications of IH NMR spectropscopy: Reaction mechanisms (electrophylic and nucleophilic substitutions, carbocations and carbanions), E,Z isomers, conformation of cyclohexane and decalins, keto-enol tautomerism, hydrogen bonding, proton exchange processes, C-N rotation, Interpretation of 1H NMR of organic molecules with examples. Dynamic NMR spectroscopy.

Unit 4

13C NMR Spectroscopy and 2D NM spectroscopy (12 hours)

Introduction, Correlation chart for 13C chemical shift, Proton-coupled 13C spectra, Proton-decoupled 13C spectra, NOE effects, Structural applications of 13C NMR, Fundamentals and applications of DEPT technique, Introduction to 2-D NMR spectroscopic techniques – 1H-1H COSY, 1H-13C COSY, HMBC and HSQC. 2D and solid state NMR. Application of 2-D NMR spectroscopy for structure elucidation. Introduction to 3D NMR.  

Electron Spin Resonance – Theory – electron spin, magnetic moment, electron spin resonance, hyperfine structure, overview of line width and anisotropy. Dynamic ESR. Triplet state in ESR. Double resonance techniques. ESR spectra of organic compounds.

Unit 5

Mass Spectrometry (14 hours)

Elemental analysis, empirical formula, molecular formula, Molecular mass, nominal mass, Exact mass, Index of hydrogen deficiency. The technique of Mass Spectrometry: Molecular ion, ion production methods (EI). Over view of Soft ionization methods, HRMS and formula mass, LC-MS, GC-MS. MS- MS, Fragmentation pattern and Mass spectra of organic functional groups. Nitrogen and ring rules, Rule of thirteen, McLafferty rearrangement.

General Introduction to Mossbauer spectroscopy and Photoelectron spectroscopy (PES).   

Structural Elucidation of Organic Compounds – Interpretation of spectroscopic data of unknown compounds, Application of UV-Vis, MS, IR and NMR spectroscopic techniques for solving structure of organic molecules.

Text Books / References

TEXTBOOKS

  1. Colin N. Banwell and Elaine M. McCash,‘Fundamentals of Molecular Spectroscopy’, 4th Edition, Tata McGraw Hill, 2007.
  2. Kemp, Organic Spectroscopy, 3rd Edition, McMillan International Higher Education
  3. L. Pavia, G.M. Lampman ,G.A. Kriz, and J.R. Vyvyan, Introduction to Spectroscopy, 5th Edition, Brooks-Cole, 2009
  4. M. Barrow, ‘Introduction to Molecular Spectroscopy’, McGraw Hill,1962.
  5. M. Silverstein, F.X. Webster, D.J. Kiemle, Spectroscopic identification of organic molecules, 8th Edition, 2014, John Wiley
  6. S. Kalsi, Spectroscopy of OrganicCompounds: NewAge International Pvt Ltd 6thedition, 2016

REFERENCES

  1. Hollas, J.M., Modern Spectroscopy, John Wiley & Sons, Fourth Edition, 2004
  2. Keeler, Understanding NMR spectroscopy, Wiley, 2009
  3. A. Skoog, F. J. Hollerand S. R. Crouch, ‘Principles of Instrumental Analysis’,6th Edition, Thomson Brooks/Cole, 2007.
  4. Kemp, NMR in Chemistry, McMillan, 1988
  5. E. Wertzand J. R. Bolton Electron Spin Resonance, Springer Science

Objectives and Outcomes

Course Outcome:

  • CO1: Apply the principles of UV-Visible spectroscopy to interpret electronic spectra of organic molecules and to predict the position of absorption peaks.
  • CO2: Explain the principles and application of vibrational spectroscopy to obtain structure and properties of organic compounds.
  • CO3: Describe the principles and applications of various NMR techniques and ESR spectroscopy to elucidate structure of organic molecules.
  • CO4: Interpret mass spectra, including fragmentation patterns, isotopic distributions and apply them to determine molecular structure and formula. 
  • CO5: Apply knowledge from multiple spectroscopic techniques to solve structural elucidation problems of unknown organic compounds.

CO-PO Mapping:

PO/PSO PO1 PO2 PO3 PO4 PO5 PO6 PO7 PO8 PO9 PO10 PO11 PO12 PSO1 PSO2 PSO3 PSO4
CO                                
CO1 2 3 1 2 3 1
CO2 2 3 1 2 3 1
CO3 2 3 1 2 3 1
CO4 2 3 1 2 3 1
CO5 3 1 2 2 3 1

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