Concerted reaction: Difference between revisions
Jump to navigation
Jump to search
imported>Tom.Reding m +{{Authority control}} (1 ID from Wikidata); WP:GenFixes & cleanup on |
imported>OAbot m Open access bot: url-access=subscription updated in citation with #oabot. |
||
| Line 2: | Line 2: | ||
[[File:Sn2EtCl+bromide.png|thumb|[[SN2|S{{sub|N}}2]] reaction of a [[bromide ion]] with [[chloroethane]] showing the concerted nature of the reaction, the transition state and the predictable [[stereochemistry]] through [[Walden inversion]].]] | [[File:Sn2EtCl+bromide.png|thumb|[[SN2|S{{sub|N}}2]] reaction of a [[bromide ion]] with [[chloroethane]] showing the concerted nature of the reaction, the transition state and the predictable [[stereochemistry]] through [[Walden inversion]].]] | ||
In [[chemistry]], a '''concerted reaction''' is a [[chemical reaction]] in which all [[Chemical bond|bond]] breaking and bond making occurs in a single [[Reaction step|step]]. [[Reactive intermediate]]s or other unstable high energy intermediates are not involved.<ref>Carey, Francis A.; Sundberg, Richard J.; (1984). Advanced Organic Chemistry Part A Structure and Mechanisms (2nd ed.). New York N.Y.: Plenum Press. {{ISBN|0-306-41198-9}}.</ref><ref>{{Cite journal|url = http://goldbook.iupac.org/CT07011.html|title = IUPAC Gold Book - concerted reaction|doi = 10.1351/goldbook.CT07011|date = 24 February 2014|accessdate = 12 April 2014|publisher = [[IUPAC]]|doi-access = free}}</ref> Concerted [[reaction rate]]s tend not to depend on [[solvent]] [[Chemical polarity|polarity]] ruling out large buildup of [[electrical charge|charge]] in the [[transition state]]. The reaction is said to progress through a '''concerted mechanism''' as all bonds are formed and broken ''in concert''. [[Pericyclic]] reactions, the [[SN2|S{{sub|N}}2]] reaction, and some [[Rearrangement reaction|rearrangements]] - such as the [[Claisen rearrangement]] - are concerted reactions. | In [[chemistry]], a '''concerted reaction''' is a [[chemical reaction]] in which all [[Chemical bond|bond]] breaking and bond making occurs in a single [[Reaction step|step]]. [[Reactive intermediate]]s or other unstable high energy intermediates are not involved.<ref>Carey, Francis A.; Sundberg, Richard J.; (1984). Advanced Organic Chemistry Part A Structure and Mechanisms (2nd ed.). New York N.Y.: Plenum Press. {{ISBN|0-306-41198-9}}.</ref><ref>{{Cite journal|url = http://goldbook.iupac.org/CT07011.html|title = IUPAC Gold Book - concerted reaction|doi = 10.1351/goldbook.CT07011|date = 24 February 2014|accessdate = 12 April 2014|publisher = [[IUPAC]]|doi-access = free|url-access = subscription}}</ref> Concerted [[reaction rate]]s tend not to depend on [[solvent]] [[Chemical polarity|polarity]] ruling out large buildup of [[electrical charge|charge]] in the [[transition state]]. The reaction is said to progress through a '''concerted mechanism''' as all bonds are formed and broken ''in concert''. [[Pericyclic]] reactions, the [[SN2|S{{sub|N}}2]] reaction, and some [[Rearrangement reaction|rearrangements]] - such as the [[Claisen rearrangement]] - are concerted reactions. | ||
The rate of the S<sub>N</sub>2 reaction is second order overall due to the reaction being [[bimolecular]] (i.e. there are two molecular species involved in the [[rate-determining step]]). The reaction does not have any intermediate steps, only a [[transition state]]. This means that all the bond making and bond breaking takes place in a single step. In order for the reaction to occur both molecules must be situated correctly. | The rate of the S<sub>N</sub>2 reaction is second order overall due to the reaction being [[bimolecular]] (i.e. there are two molecular species involved in the [[rate-determining step]]). The reaction does not have any intermediate steps, only a [[transition state]]. This means that all the bond making and bond breaking takes place in a single step. In order for the reaction to occur both molecules must be situated correctly. | ||
Latest revision as of 11:56, 24 June 2025
In chemistry, a concerted reaction is a chemical reaction in which all bond breaking and bond making occurs in a single step. Reactive intermediates or other unstable high energy intermediates are not involved.[1][2] Concerted reaction rates tend not to depend on solvent polarity ruling out large buildup of charge in the transition state. The reaction is said to progress through a concerted mechanism as all bonds are formed and broken in concert. Pericyclic reactions, the SN2 reaction, and some rearrangements - such as the Claisen rearrangement - are concerted reactions.
The rate of the SN2 reaction is second order overall due to the reaction being bimolecular (i.e. there are two molecular species involved in the rate-determining step). The reaction does not have any intermediate steps, only a transition state. This means that all the bond making and bond breaking takes place in a single step. In order for the reaction to occur both molecules must be situated correctly.
References
- ↑ Carey, Francis A.; Sundberg, Richard J.; (1984). Advanced Organic Chemistry Part A Structure and Mechanisms (2nd ed.). New York N.Y.: Plenum Press. Template:ISBN.
- ↑ Script error: No such module "Citation/CS1".