Lecture

Electrophilic Substitution: Mechanisms and Selectivity

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In course

CH-234: Organic functions and reactions II

To develop basic understanding of the reactivity of aromatic and heteroaromatic compounds. To develop a knowledge of a class of pericyclic reactions. To apply them in the context of the synthesis. ...

Description

This lecture delves into the concepts of electrophilic substitution reactions, focusing on mechanisms and selectivity. The instructor starts by questioning the students about the importance of the course and then proceeds to discuss various reactions such as nitration, sulfonation, and chloromethylation. The lecture covers the formation of sigma complexes, resonance structures, and the impact of electron-donating and electron-withdrawing groups on reaction selectivity. The instructor emphasizes the relationship between reactivity and selectivity, highlighting the role of reaction conditions, temperature, and solvents. The lecture concludes with a discussion on the factors influencing selectivity, including steric hindrance and the presence of multiple directing groups.

Instructors (2)

Felix Daniel Bobbink

Nicolai Cramer

Nicolai Cramer was born in Stuttgart, Germany; he studied chemistry at the University of Stuttgart where he graduated in 2003, and earned his PhD in 2005 under the guidance of Professor Sabine Laschat. After a research stage at Osaka University, Japan, he joined the group of Professor Barry M. Trost at Stanford University as a postdoctoral fellow in 2006. From 2007 on, he worked on his habilitation at the ETH Zurich associated to the chair of Professor Erick M. Carreira and recieved the venia legendi in 2010. In 2010, he started as Assistant Professor at the EPF Lausanne and was promoted to Associate Professor in 2013 and to Full Professor in 2015. His main research program encompasses enantioselective metal-catalyzed transformations and their implementation for the synthesis of biologically active molecules. Author profile (Angew. Chem. Int. Ed.) CV

Official source

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.

Reaction mechanism

In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical reaction occurs. A chemical mechanism is a theoretical conjecture that tries to describe in detail what takes place at each stage of an overall chemical reaction. The detailed steps of a reaction are not observable in most cases. The conjectured mechanism is chosen because it is thermodynamically feasible and has experimental support in isolated intermediates (see next section) or other quantitative and qualitative characteristics of the reaction.

Resonance

Resonance describes the phenomenon of increased amplitude that occurs when the frequency of an applied periodic force (or a Fourier component of it) is equal or close to a natural frequency of the system on which it acts. When an oscillating force is applied at a resonant frequency of a dynamic system, the system will oscillate at a higher amplitude than when the same force is applied at other, non-resonant frequencies. Frequencies at which the response amplitude is a relative maximum are also known as resonant frequencies or resonance frequencies of the system.

Aromaticity

In chemistry, aromaticity means the molecule has cyclic (ring-shaped) structures with pi bonds in resonance (those containing delocalized electrons). Aromatic rings give increased stability compared to saturated compounds having single bonds, and other geometric or connective non-cyclic arrangements with the same set of atoms. Aromatic rings are very stable and do not break apart easily. Organic compounds that are not aromatic are classified as aliphatic compounds—they might be cyclic, but only aromatic rings have enhanced stability.

Electron counting

In chemistry, electron counting is a formalism for assigning a number of valence electrons to individual atoms in a molecule. It is used for classifying compounds and for explaining or predicting their electronic structure and bonding. Many rules in chemistry rely on electron-counting: Octet rule is used with Lewis structures for main group elements, especially the lighter ones such as carbon, nitrogen, and oxygen, 18-electron rule in inorganic chemistry and organometallic chemistry of transition metals, Hückel's rule for the π-electrons of aromatic compounds, Polyhedral skeletal electron pair theory for polyhedral cluster compounds, including transition metals and main group elements and mixtures thereof, such as boranes.

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