Organic Applied Chemistry

Applied Organic Chemistry requires to have some knowledge in chemistry related to the programs taught in secondary grade, which include the subjects described here, namely, atoms electronic distribution, chemical bonding, atomic and molecular orbitals, periodic table and elements’ properties.

The theoretical classes aim at the detailed presentation of the program, using an expositive-active methodology. Theoretical classes allow the students to acquire in-depth knowledge in the addressed aspects of Chemistry, establishing bridges between different topics. Contents are exposed asking for a constant intervention of the students.

Practical component allow to implement, at an experimental level, the themes studied in the various theoretical aspects of the discipline through laboratory work of an appropriate level, including synthesis, and identification of organic compounds.

Students should acquire the following knowledge and skills:

–          Understand nomenclature rules, being able to establish the IUPAC names and/or the structures for the compounds of the studied classes

–          Know the physical and chemical properties of the organic compounds

–          Understand the chemical reactions for each group of compounds studied

–          Establishing the reactions’ mechanisms

–          Understand concepts of isomerism and conformations.

The main objective of Applied Organic Chemistry is the comprehension of the organic molecules structure, their chemicals and physical properties and their reactivity. The acquisition of knowledge about the main reactions in Organic Chemistry, aims to give the students the skills to develop pharmaceuticals’ synthetic processes. Therefore, the students should be ready to know the main organic compounds families, including their nomenclature and their most important reactions. It will also be important to acquire knowledge in what respects conformations and isomerism of each organic molecule as well the involved chemical bonds.

Alkanes: general features, isomerism, carbon and hydrogen classes, alkyl groups, IUPAC nomenclature, physical properties, conformations (eclipsed conformation, staggered conformation), tridimensional representations (Newman projections, sawhorse projection), stereochemistry (chirality, chiral carbon).

Cycloalkanes: main features, conformations (chair and boat), axial and equatorial bonds, estereoisomerism (cis/trans isomerism).

Alkanes main reactions: halogenation, combustion, pyrolysis. Mechanism of the halogenation reaction.

Alkenes: general features, physical properties, isomers, E/Z isomerism, preference rules for the E/Z configuration, IUPAC nomenclature.

Cycloalkenes: IUPAC nomenclature.

Alkenes main reactions: alkenes preparation reactions (elimination reactions – dehydrohalogenation of alkyl halides, alcohol dehydration): reactions with alkenes (addition reactions – hydrogen halides addition, sulfuric acid addition, water addition, halogens addition, hydrogen addition); Markovnikov’s Rule. Mechanisms of all the mentioned reactions.

Alkynes: main features, physical properties, IUPAC nomenclature. Alkynes main reactions: hydrogen addition, hydrogen halides addition, water addition, ceto-enolic tautomerism, halogens addition. Mechanisms of all the mentioned reactions.

Alkyl halides: main features, physical properties, IUPAC nomenclature. Main reactions of alkyl halides: Grignard reagent preparation, substitution reactions (SN1 and SN2 mechanisms), elimination reactions (dehydrohalogenation). Mechanisms for all the mentioned reactions.

Aromatic compounds: main features, physical properties, IUPAC nomenclature, aromaticity, Huckel’s rule. Aromatic compounds main reactions: nitration, halogenation, sulfonation, Friedel-Crafts. Mechanisms for all the mentioned reactions.

Aldehydes and Ketones: main features, physical properties, IUPAC nomenclature. Aldehydes preparation reactions: primary alcohols oxidation, methylbenzene oxidation, acid chlorides reduction. Ketones preparation reactions: secondary alcohols oxidation, Friedel-Crafts. Aldehydes and ketones main reactions: oxidation, reduction, nucleophilic addition (water addition, Grignard reagent addition, cyanide addition, ammoniac derivates addition, alcohols addition, aldol condensation, Cannizzaro’s reaction.

Alcohols and Ethers: main features, physical properties, IUPAC nomenclature. Alcohols preparation reactions: alcohols substitution, reduction of carbonyl compounds, reduction of acids and esters, aldol condensation. Alcohols’ reactions: reaction with hydrogen halides, reactions with acids, oxidation, dehydration. Reactions of ethers preparation: dehydration of alcohols, Williamson synthesis. Ethers’ reactions: treatment with acids. Mechanisms for all the mentioned reactions.

Carboxylic acids: main features, physical properties, IUPAC nomenclature. Preparation of carboxylic acids reactions: primary alcohols oxidation, aldehydes oxidation. Alkenes oxidation, alkylbenzenes oxidation, methylketones oxidation, Grignard reagent carbonation, hydrolysis. Reactions with carboxylic acids: salts formation, functional derivates conversion, substitution reactions (Hell-Volhard-Zelinskiy reaction), acids reduction, Grignard’s reaction. Mechanisms for all the mentioned reactions.

Carbohydrates: main features, physical properties, monossacharides’ configuration, optical activity, racemic mixtures.

NAO

Primary bibliography (existing on the library)

CAREY, F.A., Organic Chemistry, 6nd ed, New york, McGraw-Hill, 2006

MORRISON R., BOYD R., Química Orgânica, 13.ª edição, Lisboa, Fundação Calouste Gulbenkian, 1996

Secondary bibliography (other recommended bibliography)

ALLINGER N., CAVA M., JONGH D., JOHNSON C., LEBEL N., STEVENS C., Química Orgânica, 2.ª edição, Rio de Janeiro, Editora Guanabara Koogan S.A., 1978

IUPAC, Guia IUPAC para a nomenclatura de compostos orgânicos, Lidel, 2002

TOMÉ, A., Introdução à nomenclatura dos compostos orgânicos, 1ª Edição, Lisboa, Escolar Editora, 2010