Organic Chemistry

The organic chemistry module in S4 in L2 deals with the electronic, acid-base properties and reactivity of aromatic compounds of benzene, phenol and aniline derivatives. The reaction mechanisms concerning nucleophilic and electrophilic substitution reactions in aromatic chemistry will be particularly addressed. This course is a continuation of the basics acquired in L1 and the first semester of L2.

These courses should enable students to master the electronic effects, acidity and basicity of organic compounds and the reactivity of aromatic compounds derived from benzene, phenol and aniline.

Students enrolled in this module should have previously taken basic organic chemistry courses covering the electronic effects and reactivity of the main functional groups.

Recommended prerequisites: mastering the basic notions related to the electronic effects of organic molecules and the consequences on the acid-base properties and the reactivity of the main functional groups studied in the first semester in the framework of the UE HAC301C.

Final examination

Course outline

1.-Hybridization, delocalization and aromaticity.

1.1 Hybridization

1.1.a.-Introduction

1.1.b.-Hybridization of the atomic orbitals of the carbon atom

1.1.c.-Hybridization of the atomic orbitals of nitrogen and oxygen atoms

1.2 -Delocalization

            1.3 Aromaticity

                        1.3.a.-Benzene

                        1.3.b.-Heteroaromatic compounds

2. acidity, basicity and pKa

            2.1 Acidity

                        2.1.a.-The pKaof an acid

                        2.1.b.-Strength of an acid

                                2.1.b.1.-Influence of mesomeric effects

                                2.1.b.2.-Influence of the nature of the element which carries the negative charge

-carbonaceous acids

-Nitrogenous acids

                                    2.1.b.3.-Influence of inductive effects

                                2.1.b.4.-Influence of hybridization

            2.2.-Basicity

                        2.2.a.-The pKaof a base

                        2.2.b.-Loaded bases

                        2.2.c.-Nitrogenous neutral bases

                                2.2.c.1.-Effects that vary the electronic density on the nitrogen atom

                                2.2.c.2-Aniline, amides, amidines, guanidines, pyridine, pyrrole and imidazole

                        2.2.d.-Neutral oxygenated bases

                        2.2.e.-The choice of the solvent

3-Aromatic electrophilic substitution

            3.1-Benzene derivatives, phenol and aniline. Nomenclature

            3.2 The bromination of benzene

            3.3 Mechanism of the aromatic electrophilic substitution

            3.4 Benzene nitration

            3.5 Sulfonation of benzene

            3.6 Alkylation and acylation of Friedel and Crafts

            3.7 Electrophilic substitution on phenols

            3.8 Electrophilic substitution on aniline

            3.9 Alkylbenzenes

            3.10.-Electroattractant substituents

            3.11.-Halogens as substituents

            3.12.-Mono or polysubstitution?

            3.13.-Presence of several substituents

            3.14 Sulfonation of phenols and anilines

            3.15.-The diazo coupling. Synthesis of azo dyes

            3.16 Friedel and Crafts alkylation of phenol and aniline

4-Aromatic nucleophilic substitution

            4.1_SN2on C ^sp2 is impossible

            4.2 The addition-elimination mechanism

            4.3 The_SN1mechanism of aromatic nucleophilic substitution: diazonium compounds

            4.4 The benzyne mechanism

5 -Hydrogenation of benzene and its derivatives

            5.1 Catalytic hydrogenation

            5.2 Birch reduction