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How can free-radical halogenation of an alkane produce an alkyl halide?
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organohalogen compound
Vinyl chloride is an organohalogen compound that has important industrial applications. When treated with certain catalysts, vinyl chloride monomers undergo polymerization and form the larger compound known as polyvinyl chloride, or PVC. PVC is used in the manufacture of numerous products, including packaging films and water pipes.
Free-radical halogenation is a method used to synthesize alkyl halides from alkanes. This process is a chain reaction typically initiated by ultraviolet light, which facilitates the following steps:1
- Chain-initiation: The reaction begins when a halogen molecule (such as ) absorbs energy and dissociates into two highly reactive halogen radicals.1
- Chain-propagation: A halogen radical collides with an alkane molecule, abstracting a hydrogen atom to form a hydrogen halide and an alkyl radical. This alkyl radical then reacts with another halogen molecule to produce the desired alkyl halide and regenerate a halogen radical, which continues the cycle.1
- Chain-termination: The process concludes when reactive radicals collide and combine, such as when two alkyl radicals form a larger alkane or when an alkyl radical combines with a halogen radical to yield the final alkyl halide product.1
This method is one of the primary ways to prepare alkyl chlorides and bromides.2