Organic Analysis

Code

Course teacher

Associate teachers

Status of the course

Course objectives

The aim is to teach students the methods for isolation, purification and identification of diferent organic compounds classess by interpreting spectra obtained by modern spectroscopic techniques.

Course enrolment requirements and entry competences required for the course

Organic chemistry

Learning outcomes expected at the level of the course (4 to 10 learning outcomes)

After completing the course, the student will become familiarized with the major concepts of organic analysis, which includes:
- isolating different classes of organic compounds from complex mixtures
- selection of appropriate spectroscopic methods
- combining individual spectroscopic methods for structure elucidation;
- the use of spectroscopic methods to monitor the reaction process;
- application of acquired knowledge in research projects.

Course content broken down in detail by weekly class schedule (syllabus)

 Lectures and seminars (L+S):
1. Classical methods of analysis. (12 + 4)
Biological samples. Reaction products. Commercial samples. Processing of the sample, isolation and concentration. Separation based on solubility, volatility, and the acid-base properties. Separation of the enantiomers. Polarimetry.
2. Chromatographic separation (TLC, GC, HPLC). (1 + 0 )
3. Molecular formulas and what can be learned from them? (0.5 + 1)
Molecular formulas. Index of hydrogen deficiency. The rule of thirteen.
I. Partial exam (written, 1hour and 30 min)
4. Spectroscopy analysis methods. (0.5 + 0)
Spectroscopic techniques used in organic compound structure elucidation.
5. Mass spectrometry (MS). (3 + 1.5)
Theory, instrumentation, and techniques. Isotopic masses. Isotopic abundances, and high-resolution mass spectrometry (HRMS). Fragmentation in EIMS: influence of functional groups on fragmentation. Examples of different classes of organic compounds.
6. Ultraviolet and visible spectroscopy (UV/Vis) (3 + 1)
Electromagnetic spectra. The nature of electronic excitations. The origin of UV band structure. Principles of absorption spectroscopy. Presentation of spectra. Solvents. What is a chromophore. Effect of conjugation. What to look for in ultraviolet spectra. Examples of different classes of organic compounds.
7. Infrared spectroscopy (IR) (4 + 1.5)
Introduction, Theory, instrumentation, and sample preparation. C,H,O-containing functional groups. Effect of ring size, conjugation and electron-withdrawing groups. Examples of different classes of organic compounds.
8. Nuclear magnetic resonance spectroscopy (NMR). (6 + 2)
Basic concepts. 1H NMR Chemical shifts. Spin-Spin Coupling. Magnetic anizotropy. 13C NMR Chemical shifts. Aromatic compounds – substituted benzene rings. Homotopic, enantiotopic, and diastereotopic systems. 2D NMR spectroscopy. Examples of different classes of organic compounds.
9. Combined structure problems (0 + 4)
II. Partial exam (written, 2 hours)
III. Partial exam (oral, 30 min)
 Laboratory exercises (E)
1. Separation of the water-insoluble mixtures. (5)
2. Separation of the water-soluble mixtures. (5)
3. Racemic mixture. Isolating the enantiomers of 1-phenylethylamine by fractional crystalization. Measuring the rotation of plane-polarized light by polarimeter. (7)
4. Tests for determination of the functional groups of separated compounds. (5)
5. Influence of inter- and intra-hydrogen bonds on melting point: Determination of the melting point on the aluminum block. (2)
6. UV/VIS absorption spectroscopy. Bathochromic shift: recording absorption spectra (benzene, aniline, phenol, benzoic acid, cinnamic acid, ferulic acid) and determination of auxochrome effect (-OH, -NH2, - OCH3) and conjugation on absorption maximum, λmax. (4)
7. Recording absorption spectra and investigation of the influence of pH on the absorption bands of phenol and aniline. Study of the connection between molecular structure and absorption maxima: spectral acid-base indicators phenolphtalein and thymol blue in acidic and basic media. (4)
8. Hypsochromic effect of auxochrome on n→ π* transition of carbonyl group: Recording spectra of acetone and ethyl-acetate. (4)
9. Effect of solvent on the appearance of absorption band: the recording of UV spectra of phenol in ethanol and hexane. Influence of solvent on λmax (impact on the n → π* transition): spectra of acetone in water, hexane and ethanol. (4)
10. IR spectroscopy. I part: recording the specta of isolated compounds (benzoic acid, sorbitol, thymol, aniline, 1-pentanol, acetone). (5)
11. IR spectroscopy, II part: recording spectra of selected solids and liquids. (5)
12. Analysis of obtained IR spectry and comparison by databases available on Internet (SDBS, NIST,...). Finding and analysing other available spectra in selected databases (MS, NMR,...). (5)
13. NMR spectroscopy. Analysis of NMR spectra (1H i 13C NMR) by using SPINWORKS software. (5)

Format of instruction:

Student responsibilities

Optional literature (at the time of submission of study programme proposal)

E. Pretsch, P. Buehlmann, C. Affolter: ”Structure Determination of Organic Compounds, Tables of Spectral data”, Third Edition, Springer-Verlag Berlin Heidelberg, 2000.
H. Günzler, H.-U. Gremlich, Uvod u infracrvenu spektroskopiju, Školska knjiga Zagreb, 2006;
E. Breitmaier, Structure Elucidation by NMR in Organic Chemistry, Practical Guide, John Wiley & Sons, 2002;
I. Jerković, A. Radonić, Praktikum iz organske kemije, Udžbenici Sveučilišta u Splitu, Split, 2009.

Quality assurance methods that ensure the acquisition of exit competences

Quality assurance will be performed at three levels:
(1) University Level;
(2) Faculty Level by Quality Control Committee;
(3) Lecturer’s Level.

Other (as the proposer wishes to add)