High Quality Content by WIKIPEDIA articles! SNi or Substitution Nucleophilic internal stands for a specific but not often encountered nucleophilic aliphatic substitution reaction mechanism. A typical representative organic reaction displaying this mechanism is the chlorination of alcohols with thionyl chloride, or the decomposition of alkyl chloroformates, the main feature is retention of stereochemical configuration. Thionyl chloride first reacts with the alcohol to form an alkyl chloro sulfite, actually forming an intimate ion pair. The second step is the concerted loss of a sulfur dioxide molecule and its replacement by the chloride, which was attached to the sulfite group. The difference between SN1 and SNi is actually that the ion pair is not completely dissociated, and therefore no real carbocation is formed, which else would lead to a racemisation.

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