Alkenyl Halide: Structure, Synthesis, Reactions & Examples

Instructor: Laura Foist

Laura has a Masters of Science in Food Science and Human Nutrition and has taught college Science.

In this lesson we will learn what an alkenyl halide is, how they are made, and how they can be used. We will look at specific examples of the reactions to form alkenyl halides.

What are Alkenyl Halides?

Imagine that you wanted to go for a hike today, but noticed that it might start raining. Instead of canceling your plans you pack up your rainwear and head out for a fun day hiking. This rainwear that makes this day possible is probably made from a material called vinyl. Vinyl (or more specifically PVC) is also used in plastic pipes, synthetic leather, records (hence the name, vinyl record), insulation, and many other products. PVC is made using chloroethene, an alkenyl halide.

Chloroethene contains a carbon carbon double bond with one of the carbon atoms attache to a chlorine

An alkenyl halide is simply an alkenyl attached to a halide. An alkenyl is one of the carbon atoms participating in a double bond. A halide are members of group 17 on the periodic table, which includes fluoride, chlorine, bromide, and iodine. Alkenyl halides are also called haloalkenes.

The alkenyl is one of the carbon atoms in a carbon carbon double bond

Alkenyl halides are very stable and do not easily undergo reactions. This gives us a stable source of carbon-halides.

Synthesis of Alkenyl Halides

There are several different methods for synthesizing alkenyl halides. These methods include:

  • Start with an alkyl halide and oxidize it into an alkene

Hydrogen is removed from the alkyl halide and put onto the OH group, forming water, the halide can then be added
Alkyl halide into alkene halide

  • Start with a ketone, removing water and adding a halide

The oxygen is removed, taking two hydrogen atoms with it, forming water, a double bond is formed and the halide is added
Ketone into alkenyl halide

  • Start with an alkyne and reduce it into an alkene, adding a halide

Hydrogens are added onto the alkyne, forming an alkenyl halide
Alkyne into alkenyl halide

  • Start with an alkane with a good leaving group (such as Ph3and oxidize it, adding a halide

In this example BF 3 K is used as the good leaving group, and is replaced with a halide
Alkane good leaving group reaction

Chloroethene Reaction Examples

Let's look specifically at how chloroethene is made. There are several routes possible for making chloroethene:

  • Adding HCl to an alkyne at high temperatures

This reaction requires high temperatures in order to reduce the alkyne into an alkene and add the chlorine
Alkyne into chloroethene

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