Organic Chemistry

The organic chemistry module in S4 in L2 focuses on the electronic and acid-base properties and reactivity of aromatic compounds derived from benzene, phenol, and aniline. Reaction mechanisms involving nucleophilic and electrophilic substitution reactions used in aromatic chemistry will be discussed in particular. This course builds on the foundations acquired in L1 and the first semester of L2.

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

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

Recommended prerequisites: mastery of the basic concepts related to the electronic effects of organic molecules and the consequences on the acid-base properties and reactivity of the main functional groups covered in the first semester as part of the HAC301C course.

Final exam

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.-Offshoring

            1.3.-Aromaticity

                        1.3.a.-Benzene

                        1.3.b.-Heterocyclic compounds

2.-Acidity, basicity, andpKa

            2.1.-Acidity

                        2.1.a.-ThepKaof 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

-nitrogen acids

                                    2.1.b.3.-Influence of inductive effects

                                2.1.b.4.-Influence of hybridization

            2.2.-Basicity

                        2.2.a.-ThepKaof a base

                        2.2.b.-Charged bases

                        2.2.c.-Neutral nitrogen bases

                                2.2.c.1.-Effects that cause variations in 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.-Choice of solvent

3.-Aromatic electrophilic substitution

            3.1.-Benzene, phenol, and aniline derivatives. Nomenclature

            3.2.-Bromination of benzene

            3.3.-Mechanism of aromatic electrophilic substitution

            3.4.-Nitration of benzene

            3.5.-Sulfonation of benzene

            3.6.-Friedel-Crafts alkylation and acylation

            3.7.-Electrophilic substitution on phenols

            3.8.-Electrophilic substitution on aniline

            3.9.-Alkylbenzenes

            3.10.-Electron-withdrawing substituents

            3.11.-Halogens as substituents

            3.12.-Mono or polysubstitution?

            3.13.-Presence of multiple 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 substitution: diazonium compounds

            4.4.-The benzene mechanism

5.-Hydrogenation of benzene and its derivatives

            5.1.-Catalytic hydrogenation

            5.2.-Birch reduction