Do the solvolysis reactions of secondary substrates occur by the S N 1 or S N 2 mechanism: or something else? [Book Review]
David Bourget (Western Ontario)
David Chalmers (ANU, NYU)
Rafael De Clercq
Jack Alan Reynolds
Learn more about PhilPapers
Foundations of Chemistry 13 (2):131-143 (2011)
Primary and methyl aliphatic halides and tosylates undergo substitution reactions with nucleophiles in one step by the classic S N 2 mechanism, which is characterized by second-order kinetics and inversion of configuration at the reaction center. Tertiary aliphatic halides and tosylates undergo substitution reactions with nucleophiles in two (or more) steps by the classic S N 1 mechanism, which is characterized by first-order kinetics and incomplete inversion of configuration at the reaction center due to the presence of ion pairs. When the nucleophile is also the solvent, the substitution reaction is called a solvolysis, and both the S N 2 and S N 1 reactions now obey first-order kinetics. Schleyer and Bentley have provided solid, but not conclusive, evidence that secondary substrates undergo solvolysis by a merged mechanism, one that blends characteristics of both the S N 2 and S N 1 mechanisms. The following paper presents the history of their sustained pursuit of a merged mechanism and subsequent rebuttals to this claim. Several issues related to the philosophy and sociology of science are also discussed
|Keywords||Solvolysis reaction Two-step mechanism One-step mechanism Ion pairing Merged mechanism Solvent ionizing power Solvent nucleophilicity Kinetics α secondary isotope effects Secondary substrates Nucleophilic solvent assistance|
|Categories||categorize this paper)|
Setup an account with your affiliations in order to access resources via your University's proxy server
Configure custom proxy (use this if your affiliation does not provide a proxy)
|Through your library|
References found in this work BETA
Roald Hoffmann, Vladimir I. Minkin & Barry K. Carpenter (1997). Ockham's Razor and Chemistry. Hyle 3 (1):3 - 28.
Robert Lewis & J. M. Ziman (1987). Book Reviews. [REVIEW] Minerva 25 (4):513-522.
Citations of this work BETA
No citations found.
Similar books and articles
A. Korobov (2005). Simple Chemical Reactions in the Solid State: Towards Elaborating a Conception. [REVIEW] Foundations of Chemistry 7 (3):307-314.
Erik Krabbe & Jan van Laar (2011). The Ways of Criticism. Argumentation 25 (2):199-227.
Adrian Wüthrich (2012). Eating Goldstone Bosons in a Phase Transition: A Critical Review of Lyre's Analysis of the Higgs Mechanism. [REVIEW] Journal for General Philosophy of Science 43 (2):281-287.
Robert N. Brandon (1984). Grene on Mechanism and Reductionism: More Than Just a Side Issue. PSA: Proceedings of the Biennial Meeting of the Philosophy of Science Association 1984:345 - 353.
Jozef Šima (2013). Redox Reactions: Inconsistencies in Their Description. [REVIEW] Foundations of Chemistry 15 (1):57-64.
Daniel J. Nicholson (2012). The Concept of Mechanism in Biology. Studies in History and Philosophy of Science Part C 43 (1):152-163.
Lisa Downing (1998). The Status of Mechanism in Locke's Essay. Philosophical Review 107 (3):381-414.
Geert Jan M. Klerk (1979). Mechanism and Vitalism. A History of the Controversy. Acta Biotheoretica 28 (1).
Fiona Macpherson (2012). Cognitive Penetration of Colour Experience: Rethinking the Issue in Light of an Indirect Mechanism. Philosophy and Phenomenological Research 84 (1):24-62.
Jaakko Kuorikoski (2009). Two Concepts of Mechanism: Componential Causal System and Abstract Form of Interaction. International Studies in the Philosophy of Science 23 (2):143 – 160.
James G. Tabery (2004). Synthesizing Activities and Interactions in the Concept of a Mechanism. Philosophy of Science 71 (1):1-15.
Aarre Laakso & Paco Calvo (2011). How Many Mechanisms Are Needed to Analyze Speech? A Connectionist Simulation of Structural Rule Learning in Artificial Language Acquisition. Cognitive Science 35 (7):1243-1281.
Robert A. Skipper & Roberta L. Millstein (2005). Thinking About Evolutionary Mechanisms: Natural Selection. Studies in History and Philosophy of Biological and Biomedical Sciences 36 (2):327-347.
James Tabery (2004). Synthesizing Activities and Interactions in the Concept of a Mechanism. Philosophy of Science 71 (1):1-15.
Added to index2011-07-12
Total downloads7 ( #216,593 of 1,692,428 )
Recent downloads (6 months)1 ( #184,284 of 1,692,428 )
How can I increase my downloads?