Organic Chemistry

The organic chemistry module in the fourth semester of the second year focuses on the electronic and acid-base properties, as well as the reactivity, of aromatic compounds derived from benzene, phenol, and aniline. Particular attention will be given to the reaction mechanisms involved in nucleophilic and electrophilic substitution reactions in aromatic chemistry. This course builds on the foundational knowledge acquired in the first year and during the first semester of the second year.

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

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

Recommended prerequisites: a solid understanding of the basic concepts related to the electronic effects of organic molecules and their impact 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.—Heteroaromatic Compounds

2. Acidity, Basicity, andpKa

            2.1.-Acidity

                        2.1.a.—ThepKaof an acid

                        2.1.b.—Acid Strength

                                2.1.b.1.—Influence of mesomeric effects

                                2.1.b.2.—Effect of the nature of the element carrying the negative charge

-carboxylic acids

-nitrogenous acids

                                    2.1.b.3.—Influence of Inductive Effects

                                2.1.b.4.—Effect of hybridization

            2.2.-Basicity

                        2.2.a.—ThepKaof a base

                        2.2.b.—Loaded bases

                        2.2.c.—Neutral nitrogenous bases

                                2.2.c.1.—Effects that cause the electron density on the nitrogen atom to vary

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

                        2.2.d.—Neutral oxygenated bases

                        2.2.e.—Selection of the 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.—Electro-attracting substituents

            3.11.—Halogens as Substituents

            3.12.—Mono- or poly-substitution?

            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 a^sp² carbon 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