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SN1 reaction : ウィキペディア英語版
SN1 reaction

The SN1 reaction is a substitution reaction in organic chemistry. "SN" stands for nucleophilic substitution and the "1" represents the fact that the rate-determining step is unimolecular.〔L. G. Wade, Jr., ''Organic Chemistry'', 6th ed., Pearson/Prentice Hall, Upper Saddle River, New Jersey, USA, 2005〕 Thus, the rate equation is often shown as having first-order dependence on electrophile and zero-order dependence on nucleophile. This relationship holds for situations where the amount of nucleophile is much greater than that of the carbocation intermediate. Instead, the rate equation may be more accurately described using steady-state kinetics. The reaction involves a carbocation intermediate and is commonly seen in reactions of secondary or tertiary alkyl halides under strongly basic conditions or, under strongly acidic conditions, with secondary or tertiary alcohols. With primary alkyl halides, the alternative SN2 reaction occurs. In inorganic chemistry, the SN1 reaction is often known as the ''dissociative mechanism''. This dissociation pathway is well-described by the cis effect. A reaction mechanism was first proposed by Christopher Ingold et al. in 1940. This reaction does not depend much on the strength of the nucleophile unlike the SN2 mechanism.
==Mechanism==
An example of a reaction taking place with an SN1 reaction mechanism is the hydrolysis of tert-butyl bromide with water forming ''tert''-butanol:
:
This SN1 reaction takes place in three steps:
* Formation of a ''tert''-butyl carbocation by separation of a leaving group (a bromide anion) from the carbon atom: this step is slow and reversible.
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:
* Nucleophilic attack: the carbocation reacts with the nucleophile. If the nucleophile is a neutral molecule (i.e. a solvent) a third step is required to complete the reaction. When the solvent is water, the intermediate is an oxonium ion. This reaction step is fast.
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* Deprotonation: Removal of a proton on the protonated nucleophile by water acting as a base forming the alcohol and a hydronium ion. This reaction step is fast.

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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