Modern methods of organic synthesis 0600-S2-PP/NS-NMSO
Lecture:
Methods of creating carbon-carbon bonds: employing lithium, magnesium, zinc, copper, and organo-boron compounds. Palladium-catalyzed coupling reactions: Suzuki, Negishi, Sonogashira, Buchwald reactions. Diels-Alder reactions, electrocyclization, and sigmatropic rearrangement. Organocatalysis: asymmetric aldol and L-proline catalyzed Mannich reaction. The synthesis of alkenes, including the Wittig and Horner-Wadsworth-Emmons reactions. The oxidation methods of alcohols and alkenes include asymmetric epoxidation of allyl alcohols by the Sharpless method and asymmetric dihydroxylation of alkenes. Selective methods of reduction and hydrogenation. Reductions with boron and aluminum compounds. Hydrogenation in the presence of homogeneous catalysts. Protecting groups in organic synthesis, protection of alcohols and amines, as well as carboxylic acids, aldehydes, and ketones.
Laboratory:
1. Hydroboration-oxidation of alpha-pinene,
2. Wittig reaction - stilbene synthesis,
3. Asymmetric reduction of ketone with borane,
4. Horner-Wadsworth-Emmons reaction - ethyl cinnamate,
5. Synthesis of phenylboronic acid,
6. Suzuki reaction - 4-acetylbiphenyl,
7. Ethyl acetoacetate reactions - ketone protection and the Grignard reaction of ester.
Total student workload
Learning outcomes - knowledge
Learning outcomes - skills
Learning outcomes - social competencies
Teaching methods
Type of course
Course coordinators
Learning outcomes
Student
W1: has in-depth knowledge of main branches of chemistry and methods of organic synthesis – K_W01, K_W02,
W2: has knowledge of synthesis and characteristics of organic compounds, catalysts, organometallic compounds, and their practical use – K_W03,
W3: knows the rules of proper experiment planning and verification of results’ reliability and advanced techniques applied in chemical processes – K_W09, K_W013,
W4: has sufficient knowledge of occupational health and safety regulations that allows to work on their own and perform unsupervised research – K_W014.
Student
U1: is able to use and capitalise on in-depth knowledge of organic synthesis and use it creatively within the range of their specialisation – K_U01,
U2: is able to prepare a workstation and plan the synthesis process of a specific compound or chemical product – K_U06,
U3: is able to find information in scientific journals and popular science magazines as well as chemical databases published in both Polish and English and to present the results of his/her work in the form of written reports – K_U08,
U4: is able to plan and carry out an experiment on their own as well as to analyse its results critically – K_U011,
U5: is able to analyse selected types of spectra (e.g. NMR, IR) and draw conclusions with regard to the structure of compounds; is able to search for and compare spectra with those collected in various databases – K_U013.
Student
K1: is aware of their knowledge and its limitations and understands the need for lifelong learning – K_K01,
K2: is able to cooperate and work in a team (assuming various roles in this team) as well as to creatively solve problems concerning research studies and chemical synthesis – K_K02,
K3: is able to specify priorities in order to solve a chemical problem posed by themselves or by other persons – K_K05,
K4: aware of the importance of being professional, recognises and appreciates intellectual honesty and integrity, and observes the code of professional ethics both in their actions and the actions undertaken by other persons – K_K06
K5: can formulate and present opinions on fundamental chemical issues and developments in organic synthesis – K_K07.
Assessment criteria
Lecture: Written examination – W1-W3, U1, U3, U5, K3-K5
Laboratory – W1-W4, U1-U5, K1-K5
Modern methods of organic synthesis unit consists of two components: lecture 20 hours and laboratory 40 hours.
Lecture - the condition for passing the exam is:
1) passing all components of the block;
2) obtaining a minimum of 50% of the points in the written exam.
Lab: The student is required to perform five exercises. The obtained results must be prepared as written reports in a laboratory notebook. The laboratory ends with a test covering the knowledge of the performed syntheses. The laboratory grade is the sum of the test scores (50%) and reports (50%). Reports are graded on a 0-10 point scale, broken down as follows:
0 - 4 points - description in the laboratory notebook of the conducted experiment, laboratory work technique, knowledge of the instructions for performing the exercise,
0 - 6 points - the results' quality, yield calculation, measurement of physicochemical constants, description of the recorded IR spectra, and conclusions.
Practical placement
Not applicable
Bibliography
1. J. Clayden, N. Greeves, S. Warren, P. Wothers, Organic Chemistry, Oxford University Press, Oxford, 2001.
2. J. Gawroński, K. Gawrońska, K. Kacprzak, M. Kwit, Współczesna synteza organiczna, PWN, Warszawa, 2004.
3. R. Bruckner, Advanced Organic Chemistry. Reaction Mechanisms, Harcourt Academic Press, San Diego, 2002.
4. J. McMurry, Chemia organiczna, PWN, Warszawa, 2000.
5. A. Vogel, Preparatyka Organiczna, WNT, Warszawa, 2006.
Additional information
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