Lecture

Organic Chemistry: Acidity Analysis and Resonance Stabilization

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In course

CH-110: Advanced general chemistry I

Le cours comporte deux parties. Les bases de la thermodynamique des équilibres et de la cinétique des réactions sont introduites dans l'une d'elles. Les premières notions de chimie quantique sur les électrons et les liaisons chimiques, exemplifiées en chim ...

Description

This lecture covers the analysis of acidity in organic molecules, focusing on the removal of protons and the factors affecting acidity such as electronegativity, hybridization, and resonance stabilization. It also discusses the importance of resonance structures in stabilizing bases and justifying acidity trends. The session includes exercises on identifying acidic bonds, determining hybridization, and drawing orbital interactions to explain acidity variations. Additionally, it explores exceptions to acidity trends, inductive effects, and the impact of atom size on basicity. The lecture concludes with a detailed examination of resonance stabilization and its role in determining the strength of acids and bases.

Instructors (7)

Marinella Mazzanti

Expertise Inorganic Chemistry, Coordination ChemistryF-elements Chemistry Teaching & PhD Past EPFL PhD Students Julie Renée Michelle Andrez, Marta Falcone, Radmila Faizova, Davide Toniolo, Luciano Barluzzi, Aurélien René Willauer, Nadir Jori, Dieuwertje Katelijn Modder, Hsueh Fang-Che, Keerthi Shivaraam Rangaraj Ananthakumar, Mikhail Batov Past EPFL PhD Students as codirector Andreichenko Andrei Courses Chemistry of f elements CH-427 The course will provide a synopsis of the chemistry of f e

Anne-Clémence Corminboeuf

Teaching & PhD PhD Students Liam Oliver Marsh, Pratham Pushparaj Deshmukh, Roel Christiaan M Raike, Thanapat Worakul, Osvaldo Hernandez Cuellar, Juliette Veronique Schleicher, Yannick Calvino Alonso, Sara Bassetta, Yuri Cho, Kelian Dietmar Marc Gaedecke, Guoyuan Liu Past EPFL PhD Students Fabrice Avaltroni, Daniel Filipe Jana, Stephan Niklaus Steinmann, Jérôme Florian Gonthier, Riccardo Petraglia, Antonio Prlj, Laurent Alexis Clément Vannay, Alberto Fabrizio, Kun-Han Lin, Boodsarin Sawatlon, Raimon Fabreg

Jérôme Waser

Jérôme Waser biography and CV's are available on the following website: http://lcso.epfl.ch/waser

Philippe Schwaller

Beat Fierz

Teaching & PhD PhD Students Paria Khalafi, Wei Cai, Pierre Alexander Miranda Herrera, Andrei Zhauniarovich, Matteo Nicolas Doudin, Zongqing Li, Enguerran Majerus, Po-Han Chang, Iana Berlina, Yuji Kamei Past EPFL PhD Students Aurore Marie-France Delachat, Sinan Kilic, Louise Catherine Bryan, Andreas Linus Bachmann, Ninad Dilip Agashe, Nora Guidotti, Maxime Nicolas Mivelaz, Kristina Makasheva, Alexandra Teslenko, Pauline Franz, Salome Riccarda Püntener, Ly Phillippe Past EPFL PhD Students as codirector Dani

Angela Steinauer

Since 2022: Head of the Laboratory of Biomolecular Engineering and Nanomedicine (LIBN), EPFL (Switzerland)2019-2021: MSCA Postdoctoral Fellow at ETHZ (Switzerland)2018: Ph.D. in Chemical Biology from Yale University (USA)2007-2012: B.Sc. & M.Sc. in Chemistry from University of Zurich (Switzerland) Teaching & PhD PhD Students Diogo Miguel De Abreu Viegas, Georges Barnikol, Oliver Dennis, Andrea Elizabeth Melgar Aguilar, Paula Oeser, Manutsawee Thanaburakorn Courses Advanced general chemistry I CH

Official source

Ontological neighbourhood

Chemistry

Inorganic chemistry: Topics in inorganic chemistry

Related concepts (32)

Acid

An acid is a molecule or ion capable of either donating a proton (i.e. hydrogen ion, H+), known as a Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis acid. The first category of acids are the proton donors, or Brønsted–Lowry acids. In the special case of aqueous solutions, proton donors form the hydronium ion H3O+ and are known as Arrhenius acids. Brønsted and Lowry generalized the Arrhenius theory to include non-aqueous solvents.

Acid–base reaction

An acid–base reaction is a chemical reaction that occurs between an acid and a base. It can be used to determine pH via titration. Several theoretical frameworks provide alternative conceptions of the reaction mechanisms and their application in solving related problems; these are called the acid–base theories, for example, Brønsted–Lowry acid–base theory. Their importance becomes apparent in analyzing acid–base reactions for gaseous or liquid species, or when acid or base character may be somewhat less apparent.

Lewis acids and bases

A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any species that has a filled orbital containing an electron pair which is not involved in bonding but may form a dative bond with a Lewis acid to form a Lewis adduct. For example, NH3 is a Lewis base, because it can donate its lone pair of electrons.

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.

Acid dissociation constant

In chemistry, an acid dissociation constant (also known as acidity constant, or acid-ionization constant; denoted K_a) is a quantitative measure of the strength of an acid in solution. It is the equilibrium constant for a chemical reaction HA A^- + H^+ known as dissociation in the context of acid–base reactions. The chemical species HA is an acid that dissociates into , the conjugate base of the acid and a hydrogen ion, .

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Jacques-Edouard Moser

Jacques-Edouard Moser is titular professor in physical chemistry and is currently directing the Group for Photochemical Dynamics (Moser Group) of EPFL. He is a graduate of the École polytechnique fédérale de Lausanne, where he received a diploma degree (MSc) in chemical engineering in 1982. After two stays in 1984 and 1985 at Concordia University in Montréal (Canada), he earned in 1986 his Ph.D. in physical chemistry at EPFL (Michael Grätzel, thesis advisor). In 1986, he joined the Eastman Kodak Corporate Research Laboratories at Rochester (NY, USA) as a postdoctoral fellow and was later associated with the NSF Center for Photoinduced Electron Transfer at the University of Rochester. Returning to Switzerland, he was appointed as a lecturer of physical chemistry at EPFL in 1992 and was awarded the habilitation and the venia legendi in 1998. He is titular professor since 2005.His research activity focuses on the study of the dynamics of photoinduced electron transfer and charge carrier separation at donor-acceptor heterojunctions and in nanostructured semiconductors. He is the author and co-author of ca 200 scientific papers (H-index 75). He currently teaches general physical chemistry to freshmen students in chemistry. He gives two classes on general- and redox photochemistry in the MSc program in chemistry and chemical engineering and the doctoral programs in energy and photonics. Jacques-E. Moser presided the Swiss Society of Photochemistry and Photophysics (1995-1998) and chaired the jury of the Grammaticakis-Neumann international prize in photochemistry (1999-2001). He was a member of the board of the Swiss Chemical Society (2007-2012). He served as a member of the standing committee of the European Photochemistry Association (1992-2000) and of the executive committee of the division for fundamental research of the Swiss Chemical Society (1999-2014). He was the director of the Section of Chemistry and Chemical Engineering of EPFL and a member of the direction of the School of Basic Sciences from 2007 to 2015.

Related concepts (32)

Acid

Acid–base reaction

Lewis acids and bases

Resonance

Acid dissociation constant