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Predict the major product for each of the following reactions:
Predict the major product for each of the following reactions
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The addition reaction between an alkyne molecule and a chlorination molecule is called alkyne chlorineination. Double addition reactions can be achieved for alkynes in general. This means that you can add two chlorine molecules to each other.
The trans phase addition of the triple bond via a chlorinum-ion intermediate is called chlorine addition to alkyne. This addition reaction is alkyne acting as HOMO and chlorine molecule as LUMO. The chlorine molecule has a partial polarization; an alkene can attack the positive charge side of the electron cloud by pushing it towards the other chloro atom.
The alkyne is located in an electron rich area, which acts as both a nucleophile and an electrophile.
We can make a tetra-chlorinated product by adding one more chlorine molecule to the Trans product.
Formation of a chloroinium ion intermediary:
The nucleophile in this case is the chloride ion. It is made from the chlorine molecule produced in step 1.
Because chlorine is a larger atom than oxygen, a nucleophile attack occurs from the back of the chloronium-ion cycle that is present in the intermediate reaction.
Step 1: The Trans product is reacted with another equivalent of chlorination and produces a tetrachlorinated alkane. This reaction follows the same mechanistic path as alkyne chlorineination.
Bromination of the given alkyne product is