Possible answer:

Free radical chlorination of 3-methyl hexane can yield seven different monochlorinated products due to the structural complexity and reactivity of this hydrocarbon. The following factors contribute to the variety of products:

Steric hindrance

The 3-methyl group on the hexane chain creates a branched structure that affects the accessibility and selectivity of the radical chlorination process. Specifically, the tertiary carbon atom next to the 3-methyl group is less reactive than the primary and secondary carbon atoms in the linear chain, due to the stronger C-H bond and the weaker radical stabilization effect. Therefore, the radical chlorine tends to attack the primary and secondary carbons more readily than the tertiary carbon. As a result, some of the products have a chlorine atom attached to the 2-methyl carbon, while others have a chlorine atom attached to one of the primary carbons or the second carbon.

Multiple sites of reaction

Due to the six carbon atoms in the hexane chain, there are several possible locations for the radical chlorine to attach and form a stable product. Depending on the site of attachment, the product may have different chemical and physical properties, such as boiling point, melting point, solubility, and reactivity. Therefore, each product may have a distinct role and use in chemistry and industry.

Formation of secondary radicals

During radical chlorination, the initial radical chlorine reacts with the hydrocarbon to form a new radical and a hydrogen chloride molecule. This new radical can then react with another molecule of the hydrocarbon or with the hydrogen chloride to form secondary radicals. These secondary radicals can lead to additional chlorination or dehydrochlorination reactions, resulting in more products and complexity.

Possible monochlorinated products

The seven possible monochlorinated products of 3-methyl hexane are:

1-chloro-3-methyl hexane (chlorine attached to the 2-methyl carbon)
2-chloro-3-methyl hexane (chlorine attached to the second carbon)
3-chloro-3-methyl hexane (chlorine attached to the tertiary carbon)
4-chloro-3-methyl hexane (chlorine attached to the primary carbon next to the 2-methyl carbon)
5-chloro-3-methyl hexane (chlorine attached to the primary carbon next to the second carbon)
6-chloro-3-methyl hexane (chlorine attached to the primary carbon next to the tertiary carbon)
2,5-dichloro-3-methyl hexane (two chlorine atoms attached to the 2-methyl and the second carbons)

Conclusion

In summary, the complexity and reactivity of 3-methyl hexane lead to the formation of seven monochlorinated products on free radical chlorination, each with a unique structure and properties. Understanding the factors that contribute to this diversity can help predict and control the outcomes of radical reactions and design more efficient and selective synthesis routes.