Britannica
Sources used in this answer
How do alkyl halides differ from vinylic halides?
Created from Britannica articles
using AI.
AI can make mistakes, so verify using Britannica articles.
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.
The primary difference between alkyl halides and vinylic halides lies in the bonding environment of the carbon atom attached to the halogen.1
- Alkyl Halides: In these compounds, the carbon atom bearing the halogen is bonded to other atoms exclusively through single bonds. They are classified as primary, secondary, or tertiary based on the degree of substitution at that carbon. Alkyl halides are characterized by their ability to undergo nucleophilic substitution reactions, which are central to their chemical utility.123
- Vinylic Halides: In these compounds, the carbon atom that bears the halogen is part of a double bond with another carbon atom.1
This structural distinction significantly impacts their reactivity. Vinylic halides are essentially unreactive toward the nucleophilic substitution reactions that are common for alkyl halides. While they can undergo elimination reactions and addition to their double bonds, many of the standard reactions used for alkyl halides occur too slowly in vinylic halides to be practical.45