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Alkene Reactions: Dichloride Formation using Cl2 and Alkenes

Chlorine (Cl2) in the presence of alkenes reacts to form dichlorides:

Alkene Reactions: Dichloride Formation using Cl2 and Alkenes image2.png

Chlorine reacts with the alkene molecule to form a vicinal dichloride (1,2-dichloride) where chlorines are added to the opposite side of each other in anti addition, giving 2 products that are enantiomers:

Anti Addition

Alkene Reactions: Dichloride Formation using Cl2 and Alkenes image4.png

Partial anti Addition

Alkene Reactions: Dichloride Formation using Cl2 and Alkenes image2.png

No stereocenters

Alkene Reactions: Dichloride Formation using Cl2 and Alkenes image3.png

The reaction mechanism is depicted below:

Alkene Reactions: Dichloride Formation using Cl2 and Alkenes image1.png

In the first step, electrons from the alkene bond react with the first chlorine to make a bond, and electrons from the first chlorine atom react with the other carbon to form another bond, forming a ring structure as an intermediate.

In the second step, the free, negatively charged chlorine , attacks the backside of the intermediate structure, causing one chlorine to finish with one type of stereochemistry and the other chlorine to finish with the opposite type of stereochemistry, resulting in an anti addition.

The reagent used for this reaction is Cl2.