Guia docente 2018_19 Facultade de Química

Contents

Topic	Sub-topic
Lesson 1. Configurational stereoisomerism	Functional groups. Three-dimensional representation of organic structures. Absolute configuration of stereogenic centres, cyclic compounds and alkenes.
Lesson 2. Reactivity of organic compounds	Acid-base reactivity of organic compounds. Reaction mechanisms: stepwise reactions. Energetic profile of a reaction. Heterolytic bond cleavage. Ionic reactions. Reaction intermediates: carbanions. Redox reactivity of organic compounds. Formal states of oxidation.
Lesson 3. Addition reactions to carbon-carbon multiple bonds	Structure and general reactivity of functional groups with carbon-carbon multiple bonds: alkenes and alkynes. Hydrogenation: heats of hydrogenation and stability of alkenes and dienes; homolytic bond cleavage; concerted reactions. Electrophilic addition reactions to alkenes. Addition of HX; reaction intermediates: carbocations; regioselectivity; electrophiles and nucleophiles. Hydration reactions; orientation and stereochemistry. Addition of halogens (X2). Dihydroxylation reactions. Addition reactions to alkynes.
Lesson 4. Aromatic substitution reactions	Structure and general reactivity of aromatic compounds. General mechanism for the electrophilic aromatic substitution reaction. Reactions with non-carbon electrophiles. Reactions with carbon electrophiles. Electrophilic aromatic substitution reactions in substituted systems: orientation and reactivity. Modulation of the reactivity of aromatic rings.
Lesson 5. Reactions of nucleophilic addition to the carbonyl group	Structure and general reactivity of the carbonyl group (aldehydes and ketones). General mechanism for the nucleophilic addition reaction. Non reversible nucleophilic additions: addition of organometallic compounds (alkynyl anions, organolithium and organomagnesium reagents); addition of stabilized carbanions; addition of hydride. Reversible nucleophilic additions: addition of oxygen and sulphur compounds (water, alcohols and thiols); addition of nitrogen compounds (amines and other nitrogen compounds); addition of hydrogen cyanide.
Lesson 6. Reactions of nucleophilic substitution at the carbonyl group	Structure and general reactivity of carboxylic acids and their derivatives. Relative reactivity of acid derivatives: basicity and electrophilic character. Non reversible addition-elimination reactions: leaving group. Reversible addition-elimination reactions: basic catalysis and acid catalysis. Reactions with water and alcohols; reactions with ammonia and amines. Structure and reactivity of nitriles. Reactions of nitriles.
Practice 1	Separation of organic compounds mixtures by using two techniques: acid-base extraction (liquid-liquid extraction) and column chromatography. Four sessions.
Practice 2	Electrophilic addition to a double bond. One session.
Practice 3	Electrophilic aromatic substitution. One session.
Practice 4	Reduction of a ketone. One session.
Practice 5	Preparation of a hydrazone. One session.
Practice 6	Hydrolysis of an ester. One session.
Practice 7	Synthesis project. Three sessions.