Organic Chemistry

The organic chemistry module in S4 in L2 focuses on the electronic, acid-base properties and reactivity of aromatic compounds of benzene, phenol and aniline derivatives. In particular, the reaction mechanisms involved in nucleophilic and electrophilic substitution reactions in aromatic chemistry will be covered. This course builds on the basic knowledge acquired in L1 and the first semester of L2.

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

Recommended prerequisites: mastery of basic concepts relating to the electronic effects of organic molecules and the consequences for the acid-base properties and reactivity of the main functional groups covered in the first semester in 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 nitrogen and oxygen atomic orbitals

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 carrying the negative charge

-carbon 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 electron 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 solvent

3 -Aromatic electrophilic substitution

            3.1-Benzene derivatives, phenol and aniline. Nomenclature

            3.2-Benzene bromination

            3.3 Mechanism of aromatic electrophilic substitution

            3.4 Benzene nitration

            3.5-Sulfonation of benzene

            3.6 Friedel and Crafts alkylation and acylation

            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.-Diazo coupling. Synthesis of azo dyes

            3.16 Friedel-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 subsititution: diazonium compounds

            4.4 The benzyne mechanism

5 - Hydrogenation of benzene and its derivatives

            5.1-Catalytic hydrogenation

            5.2-Birch reduction