The Most Popular Addition of HOCl to Alkene

In this post, we are going to learn about the markovnikov’s addition rule.

What is the mechanism for addition of HOCl to alkene?

Addition of HOCl to an alkene is done by Markovnikov’s addition rule.

What is Markovnikov’s addition rule?

When a protic acid (HX) is added to an asymmetric alkene, the acidic hydrogen attaches itself to the carbon having a greater number of hydrogen substituents, whereas the halide group attaches itself to the carbon atom which has a greater number of alkyl substituents.

To simplify the rule, it can also be stated as – “Hydrogen is added to the carbon with the most hydrogen and the halide is added to the carbon with least hydrogen”.

As a result, it means that the positive part of HX is added to carbon having more hydrogen and the negative part is added to carbon with least hydrogen, at the double bond.

How reaction occurs?

HOCl first reacts with acid to form Cl⁺ cation and water.

Alkene then reacts with Cl⁺ to form a stable carbocation. There are two possibilities for the carbocation form. One is more stable while the other is less stable.

More stable carbocation will carry out the reaction to form the major product, while the less stable carbocation will form the minor product.

After the formation of carbocation, water formed in first step attacks on carbocation and H⁺ leaves the compound which is added in first step.

What is the reaction mechanism of addition of HOCl to alkene?

Generally, the tertiary carbocation is highly stable and primary carbocation is least stable. So, secondary carbocation form in the reaction is more stable than primary carbocation.

Hence, the major product is formed by secondary carbocation while the minor product is formed by primary carbocation.

Reaction mechanism is provided in the image below:

Read More: What are easy ways of organic conversions?

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