Conversion to alkyl chlorides [SOCl2]

Conversation to alkyl chlorides [SOCl2] Definition:


Primary or secondary alcohols can be converted into alkyl chlorides through treatment with SOCl2.



Conversation to alkyl chlorides [SOCl2] Explained:


Alkyl chlorides can be obtained from primary and secondary alcohols in the presence of thionyl chloride, SOClin pyridine by simply warming. The mechanism of this reaction proceeds via an SN2 process in three steps:

STEP 1. The conversation of the hydroxyl group of alcohol into a better leaving group. A reaction of the alcohol with thionyl chloride forms an intermediate and also nucleophile (chloride ion) which is needed in the last step.

STEP 2. The intermediate formed in the previous step is deprotonated by pyridine how to get a good leaving group.

STEP 3. Nucleophilic attack of chloride ion and loss of the leaving group takes place in one step via an SN2 mechanism. The carbon-oxygen bond is broken as the carbon-chloride bond is formed.