Primary alcohols and methanol react to form alkyl halides under acidic conditions by an s n 2 mechanism. Vinyl and aryl halides react with a molar equivalent of n butyllithium in a lithium halogen exchange to generate vinyl and aryllithiums which can displace a leaving group in an electrophile and form a new carbon carbon bond. Metalation is a common way of preparing versatile organolithium reagents.
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