Advanced Organic Chemistry 310-ERS-COZE
Laboratorium (LAB) Rok akademicki 2024/25

1. J. Clayden, N. Greeves, S. Warren, P. Wothers "Organic Chemistry",

2. D. G. Morris "Stereochemistry",

3. M. B. Smith, J. March "March's Advanced Organic Chemistry"

4. J. March "Organic Chemistry: reactions, mechanisms, structure"

5. J. McMurry "Organic chemistry"

6. I. Fleming. D. Williams "Spectroscopic Methods in Organic Chemistry"

7. A. I. Vogel "Textbook of Practical Organic Chemistry"

8. L. M. Harwood, C. J. Moody "Experimental Organic Chemistry: Principles and Practice"

KP7_WG1 – Demonstrates knowledge of the types of organic reactions and is capable of discussing and graphically presenting both basic and complex organic reaction mechanisms in accordance with the current state of scientific knowledge.

KP7_WG2 – Possesses advanced knowledge in organic chemistry, enabling a detailed discussion of the structure of organic compounds (including their spatial arrangement), their physical and chemical properties, and an explanation of their reaction mechanisms. Understands methods of synthesis and identification of organic compounds.

KP7_WG7 – Has knowledge of health and safety regulations (H&S), with particular expertise in the safe handling of chemical reagents and solvents, as well as in the segregation and disposal of chemical waste. Demonstrates the ability to apply this knowledge in laboratory work and in the organization of a safe independent research workstation.

KP7_UW1 – Is capable of planning and performing scientific experiments in the field of organic compound synthesis, selecting appropriate quantities of reagents and the proper glassware and laboratory equipment.

KP7_UW2 – Is able to choose and apply appropriate measurement techniques to verify the achievement of synthetic objectives and to utilize the obtained data for determining the structure of organic compounds.

KP7_UW6 – Has acquired fundamental skills in the interpretation of IR, ¹H NMR, and ¹³C NMR spectra. Is able to compare and interpret data, applying known solutions to novel situations in organic synthesis and analysis. Can prepare a report on the conducted experiments.

KP7_KO2 – Is capable of working both independently and as part of a team. Possesses knowledge of health and safety regulations and is prepared to establish a safe working environment for themselves and other group members.

Verification methods:

KP7_WG1, KP7_WG2

verification: Written test, report on the experiment conducted.

KP7_WG7

verification: Report on the experiment conducted.

KP7_UW1, KP7_UW2, KP7_UW6

verification: Reports and written tests from laboratory exercises, ongoing assessment of performance during laboratory sessions; KP7_UW1: Quiz.

KP7_KO2

verification: Ongoing assessment of performance during laboratory sessions.

Assessment methods:

- reports and written tests from laboratory exercises, chemical equipment quiz, regular assessment of performance during laboratory exercises.

The condition for passing the laboratory is attendance at all laboratory exercises and obtaining positive grades for the quiz, report(s), and written test(s).

Detailed requirements:

1. Performing 1-2 syntheses (one-step or multi-step) from a pool of prepared experiments.

2. Checking the preparation for laboratory exercises.

3. Continuous assessment of laboratory exercise performance and adherence to health and safety regulations during its execution.

4. Evaluation of the written report on the completed exercise.

5. Written tests on the theoretical knowledge related to the performed laboratory exercise.

6. Evaluation based on a quiz at the end of the classes, designed to assess acquired practical skills.

Assessment criteria according to the approved University of Białystok Study Regulations.

Students should complete missed coursework within a timeframe agreed with the teacher.

Preparations:

1. Diels-Alder reaction of maleic anhydride and furan. Esterification of the obtained adduct using the Steglich method.

2. Synthesis of 5,6-epoxycholesterol from cholesterol.

3. Synthesis of phenylserine via condensation of benzaldehyde with glycine.

4. Synthesis of cinnamonnitrile via condensation of benzaldehyde with acetonitrile.

5. Synthesis of (S)-(+)-4-carboxy-γ-butyrolactone from L-glutamic acid. Esterification of (S)-(+)-4-carboxy-γ-butyrolactone.

6. Separation of D,L-α-phenylethylamine into enantiomers.

7. Synthesis of phenyl benzoate via the Schotten–Baumann method.

practical exercises, observation, problem-based methods, explanatory lecture