Chlorination of alkanes can produce a multitude of products. Determine the number of monochlorinated and dichlorinated products that can be obtained by chlorination of 3-methylpentane. (Consider constitutional isomers only. Do not count stereoisomers.)

Chlorination of alkanes is a reaction that takes place when the chlorine is in presence of light. This actually decomposes the chlorine, and one atom of Chlorine substracts an hydrogen from the alkane. Now, this hydrogen substracted comes usually from the most substitued carbon, because it's more stable (A tertiary carbon is more stable than a secondary carbon, and this more stable than primary).

When this happens, the other chlorine atom, goes as electrophyle in that carbon and formed the chlorinated product. Now, although a tertiary carbon is more stable, we can still have (in minor quantities) chlorinated products that comes from a secondary and primary carbon. The first picture shows the general mechanism of the chlorination, and the possible products for a monochlorinated.

The second picture shows the possible dichlorinated products, which are in higher quantities than the monochlorinated basicallu because of the variety of positions the chlorine can be. So, second picture shows all the products.