Lecture

Elimination Reactions in Organic Chemistry

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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 elimination reactions in organic chemistry, focusing on E1 and E1CB mechanisms. It explains how these reactions proceed via charged intermediates and the factors that influence the choice between elimination and substitution reactions. The instructor discusses the importance of reaction conditions, leaving groups, bases, and temperature in determining the reaction pathway. Examples of non-nucleophilic bases are provided to illustrate their role in promoting elimination reactions. The lecture emphasizes the competition between elimination and substitution reactions, highlighting the conditions that favor each pathway. It concludes by summarizing the key concepts of polar reaction mechanisms and mentioning the relevance of radical reactions in polymer science.

Instructors (3)

Holger Frauenrath

Holger Frauenrath (born in Aachen, Germany) studied chemistry at RWTH Aachen , Germany from 1992 to 1997, with a focus on synthetic organic chemistry. He performed his PhD thesis from 1998 to 2001 in the research group of Prof Hartwig Höcker at RWTH Aachen, working on a project related to the stereospecific polymerization of methacrylates as well as their copolymerization with olefins using zirconocene catalysts. Holger Frauenrath then joined the group of Prof. Sam Stupp at Northwestern University , Evanston, IL, USA, as a postdoctoral fellow supported by a Feodor Lynen fellowship of the Alexander von Humboldt Foundation . His postdoctoral research projects were centered around the supramolecular self-assembly of rod-coil molecules. Holger Frauenrath returned to Germany in 2003 and started to build his own research group at FU Berlin, funded with an Emmy Noether Grant from the German Science Foundation . In 2005, the research group moved to the Department of Materials at ETH Zurich , Switzerland, where it became a scientifcally independent part of the Polymer Chemistry Group led by Prof. A. Dieter Schlüter . Holger Frauenrath obtained his Habilitation from ETH Zurich in 2009. In 2009, Holger Frauenrath has been appointed as a professor at the Institute of Materials (IMX) of the Ecole Polytechnique Federale de Lausanne (EPFL) , Switzerland, building the new Laboratory of Macromolecular and Organic Materials (LMOM) . In the same year, Holger Frauenrath was received the prestigious European Research Council (ERC) Starting Investigator grant.

Daniel Görl

Teaching & PhD Courses Organic chemistry MSE-211 This course provides a basic foundation in organicchemistry 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 polymer synthesis. Polymer science MSE-362 Polymer science + TP MSE-360 Introduction to polymer physics and the link between chemical structure and macroscopic

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).

Official source

Ontological neighbourhood

Chemistry

Chemical reactions: Organic reactions

Related concepts (32)

Chemical reaction

A chemical reaction is a process that leads to the chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the positions of electrons in the forming and breaking of chemical bonds between atoms, with no change to the nuclei (no change to the elements present), and can often be described by a chemical equation. Nuclear chemistry is a sub-discipline of chemistry that involves the chemical reactions of unstable and radioactive elements where both electronic and nuclear changes can occur.

Organic reaction

Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions, photochemical reactions and redox reactions. In organic synthesis, organic reactions are used in the construction of new organic molecules. The production of many man-made chemicals such as drugs, plastics, food additives, fabrics depend on organic reactions.

Elimination reaction

An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one- or two-step mechanism. The one-step mechanism is known as the E2 reaction, and the two-step mechanism is known as the E1 reaction. The numbers refer not to the number of steps in the mechanism, but rather to the kinetics of the reaction: E2 is bimolecular (second-order) while E1 is unimolecular (first-order). In cases where the molecule is able to stabilize an anion but possesses a poor leaving group, a third type of reaction, E1CB, exists.

SN2 reaction

DISPLAYTITLE:SN2 reaction The SN2 reaction is a type of reaction mechanism that is common in organic chemistry. In this mechanism, one bond is broken and one bond is formed in a concerted way, i.e., in one step. The name SN2 refers to the Hughes-Ingold symbol of the mechanism: "SN" indicates that the reaction is a nucleophilic substitution, and "2" that it proceeds via a bi-molecular mechanism, which means both the reacting species are involved in the rate-determining step.

Pericyclic reaction

In organic chemistry, a pericyclic reaction is the type of organic reaction wherein the transition state of the molecule has a cyclic geometry, the reaction progresses in a concerted fashion, and the bond orbitals involved in the reaction overlap in a continuous cycle at the transition state. Pericyclic reactions stand in contrast to linear reactions, encompassing most organic transformations and proceeding through an acyclic transition state, on the one hand and coarctate reactions, which proceed through a doubly cyclic, concerted transition state on the other hand.

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