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Teaching GuideTerm Faculty of Science |
| Grao en Química |
 Subjects |
| Experimental Organic Chemistry |
| Contents |
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| Identifying Data | 2020/21 | |||||||||||||
| Subject | Experimental Organic Chemistry | Code | 610G01029 | |||||||||||
| Study programme |
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| Descriptors | Cycle | Period | Year | Type | Credits | |||||||||
| Graduate | 2nd four-month period |
Third | Obligatory | 6 | ||||||||||
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| Topic | Sub-topic |
| Presentation | Methods, programmed activities and evaluation criteria |
| Carbonyl group. Reduction reactions, synthesis of commercially interesting products |
Experiment 1a: Vainilline reduction with sodium borohydride. Experiment 1b: Methyl diantilis synthesis. |
| Alkenes, alkyl halides, alcohols and epoxides. Electrophilic addition to unsaturated systems, bimilecular nucleophilic substitution ans rearrangenments. |
Experiment 2: Stereospecific synthesis of anti-2-bromo-1,2-diphenylethanol from trans-stilbene. |
| Aromatic compounds and electrophilic aromatic substitution. Introduction to protecting groups. | Experiment 3: Synthesis of p-nitroaniline from aniline. |
| Carboxylic acid derivatives. Nucleophilic substitution through addition-elimination. |
Experiment 4a: Synthesis of ethyl acetate. Experiment 4b: Synthesis of isoamyl acetate. |
| Sustainable chemistry. Reactions without solvents. | Experiment 5: Synthesis of N-(2-hydroxy-3-methoxybenzyl)-N-p-tolylacetamide. |
| Carbonyl compounds and reactions in alpha position. | Experiment 6a: Synthesis of dibenzalacetone ((E,E)-1,5-diphenyl-1,4-pentadien-3-one) from acetone and benzaldehyde through aldol condensation. Experiment 6b: Synthesis of ketone alfa,beta-unsaturated (6-etoxicarbonyl-3,5-diphenyl-2-cyclohexanone) through Michael reactions and aldol condensation. |
| Dienes. Diels-Alder reaction | Experiment 7: Synthesis of exo- and endo-7-oxabicyclo[2.2.1]hept-5-en-2,3-dicarboxy-N-phenylimide from N-phenylmaleimide |
| Polifunctional compounds. Multistep synthesis |
Experiment 8a: Synthesis of benzylic acid from benzaldehyde. Experiment 8b: Synthesis of 3-methylcyclohexen-2-one trough Robinson annulation and decarboxylation Experiment 8c: Stereoselective reduction of benzoin adn synthesis of 4,5-diphenyl-2,2-dimethyl-1,3-dioxolan Experiment 8d: Regioselective epoxydation of (R)-carvone. Experiment 8e:Synthesis of local anesthetic benzocaine (ethyl p-aminobenzoate). |
| Organophosphorous compounds. Olefination reactions. |
Experiment 9: Synthesis of cynnamic acid through Wittig reaction. |
| Heterocyclic compounds. Synthesis. Green chemistry and pharmacologicaly interesting heterocycles. |
Experiment 10a: Synthesis of 6-methylquinolin through Skraup reaction. Experiment 10b: Synthesis of 1,6-dihydropyridines through Hantzsch reaction in solventless conditions. Práctica 10c: Synthesis of Fischer indole: preparation of 1,2,3,4-tetrahydrocarbazole. |
| Carbohydrates. Kinetic and thermodinamic control. Protecting groups. Sugars as chiral precursors. |
Experiment 11a: Synthesis of beta- and alpha-D-glucose pentaacetates. Experiment 11b: Synthesis of 2,3-O-isopropyliden-L-erithrose from L-arabinose |
| Amino acids and peptides | Experiment 12: Synthesis of methyl N-acetyl-L-prolyl-L-phenylalaninate from its amino acids. |
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