Teaching GuideTerm Faculty of Science |
Grao en Química |
Subjects |
Experimental Organic Chemistry |
Contents |
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Identifying Data | 2018/19 | |||||||||||||
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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