Lecture

Aromatic Compounds: Reactivity and Substitution

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In course

MSE-211: Organic chemistry

This course provides a basic foundation in organic chemistry and polymer chemistry, including chemical nomenclature of organic compounds and polymers, an understanding of chemical structures, chemical reaction mechanisms, as well as methods of organic and ...

Description

This lecture covers the reactivity of aromatic compounds, focusing on electrophilic addition and substitution reactions. It explains how multiple bonds in aromatic systems differ from olefins, the mechanism of electrophilic aromatic substitutions, regioselectivity, and examples of reactions such as bromination, Friedel-Crafts alkylation, and sulfonation. The lecture also discusses regioselectivity in electrophilic substitutions directed by previous substituents and the learning outcomes related to the weak nucleophilic nature of aromatic systems.

Instructors (3)

Anne-Sophie Chauvin

Web of Science Researcher ID F-4905-2011 Google Scholar page: https://scholar.google.ch/citations?user=O_HhJUEAAAAJ&hl=fr&oi=ao ORCID number is 0000-0001-9222-3866 Anne-Sophie Chauvin studied chemistry and biology at the university Paris V-René Descartes in France where she did a PhD in organic chemistry, working on mimetic complexes of the active site of Nitrile Hydratase, under the supervision of Prof. Jean-Claude Chottard. On 1999 she moved for 20 months to the University of Geneva, for a post-doctoral stay under the supervision of Prof. Alexandre Alexakis, where she focused on the determination of the absolute configuration of chiral alcohols using Organophosphorous Diamine Derivatizing Agents by 31P and 1H NMR Spectroscopy. On 2000 she joined the group of Prof Jean-Claude G. Bünzli and was appointed part-time lecturer in 2001, assuming teaching and research responsibilities. On 2006, she obtained the habilitation to direct research from the University René Descartes (HDR, Paris V, France) and since october 2007 she is Maître d'Enseignement et de Recherche at the EPFL. In 2010, she joigned the Laboratory for Photonics and Interfaces (LPI), headed by Pr. Michaël Graëtzel. Since the end of 2014, with the arrival of Dr Marinella Mazzanti at EPFL, she is back to lanthanide chemistry, dealing with coordination polymers. Her research interests concern supramolecular chemistry with the design of ligands which form water soluble complexes with luminescent lanthanides in view of biological applications. She is also interested in the synthesis of ligands and polymers for the extraction of lanthanide ions with high selectivity, and in the development of invisibke inks. She also developed organic dyes for dyes sensitized solar cells DSSC. She is now focusing on coordination polymers with luminescent properties and catalytic activity. Anne-Sophie Chauvin is involved in the teaching of General and Analytical Chemistry for students enrolled on first year in Pharmacy and Biology (UNIL): ex-cathedra courses (Chimie Générale et analytique I et II, approfondissement en chimie analytique pour pharmaciens) and exercices. She is in charge of practical sessions for students enroled in chemistry, forensic sciences, pharmacy and biology. She is elected at the FSB Faculty Council and was member of the EPFL Assembly (AE) for 6 years, until 2018. She was member of the Management committee of the Cost CM 1006 action entitled Eufen: European F-Element Network. She is Member of the Swiss Chemical Society (SCS) and Fellow of the Royal Society of Chemistry (FRSC).

Holger Frauenrath

Official source

Ontological neighbourhood

Chemistry

Chemical reactions: Organic reactions

Related concepts (30)

Nucleophilic substitution

In chemistry, a nucleophilic substitution is a class of chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule (known as the electrophile). The molecule that contains the electrophile and the leaving functional group is called the substrate.R. A. Rossi, R. H. de Rossi, Aromatic Substitution by the SRN1 Mechanism, ACS Monograph Series No. 178, American Chemical Society, 1983. .

Möbius aromaticity

In organic chemistry, Möbius aromaticity is a special type of aromaticity believed to exist in a number of organic molecules. In terms of molecular orbital theory these compounds have in common a monocyclic array of molecular orbitals in which there is an odd number of out-of-phase overlaps, the opposite pattern compared to the aromatic character to Hückel systems. The nodal plane of the orbitals, viewed as a ribbon, is a Möbius strip, rather than a cylinder, hence the name.

Substitution reaction

A substitution reaction (also known as single displacement reaction or single substitution reaction) is a chemical reaction during which one functional group in a chemical compound is replaced by another functional group. Substitution reactions are of prime importance in organic chemistry. Substitution reactions in organic chemistry are classified either as electrophilic or nucleophilic depending upon the reagent involved, whether a reactive intermediate involved in the reaction is a carbocation, a carbanion or a free radical, and whether the substrate is aliphatic or aromatic.

Nucleophilic addition

In organic chemistry, a nucleophilic addition reaction is an addition reaction where a chemical compound with an electrophilic double or triple bond reacts with a nucleophile, such that the double or triple bond is broken. Nucleophilic additions differ from electrophilic additions in that the former reactions involve the group to which atoms are added accepting electron pairs, whereas the latter reactions involve the group donating electron pairs.

Electrophilic addition

In organic chemistry, an electrophilic addition reaction is an addition reaction where a chemical compound containing a double or triple bond has a π bond broken, with the formation of two new σ bonds. The driving force for this reaction is the formation of an electrophile X+ that forms a covalent bond with an electron-rich, unsaturated C=C bond. The positive charge on X is transferred to the carbon-carbon bond, forming a carbocation during the formation of the C-X bond.

Related lectures (61)

Organic Chemistry: Electrophilic Substitution

Explores strategies for total synthesis of complex molecules through electrophilic substitution reactions on aromatic compounds, discussing challenges and applications.

Electrophilic Substitution: Mechanisms and Selectivity

Explores electrophilic substitution reactions, emphasizing mechanisms and selectivity in aromatic compounds.

Organic Chemistry: Reaction Mechanisms

Explores organic reaction mechanisms, thermodynamics, kinetics, and reaction profiles in organic chemistry.

Electrophilic Reactions in Organic Chemistry

Explores reactions of olefins with electrophiles, regioselectivity in additions, and stereoselectivity in electrophilic additions.

Aromatic Compounds: Coupling Agents and Selectivity