# Reaction of octahydroazecine with iodine crystals [closed]

I really don’t understand why the following reaction would take place first of all.

So this is a sub part of a question wherein we have to compare the basicity of the compounds formed through some reactions. So, I got the rest 3 of them but I have no clue about this one.

My concerns are..

• Why would $$\ce{I2}$$ react in absence of any oxidising agent or catalyst?
• Should the presence of $$\ce{N}$$ influence the reaction.

• Is this reaction feasible?

Ans -

• You don't need an oxidizing agent, as the iodine I2 is the oxidant you are looking for. And the Nitrogen atom is necessary, because it has an available doublet. – Maurice Feb 2 at 14:21
• @Maurice Thanks for the response but it does answer my question. First of all in halogens iodine does not react with alkenes directly ( I have been taught this , in simple words it's difficult to force it to react )...it can react in presence of a solvent or such like THF or some others .. ( I found this while doing some research) ..but since none of them is here why would it react ...and moreover what is the mechanism of the reaction? – Muskaan Feb 2 at 15:31
• If you think iodine does not react with alkenes you have been misled - it does. The solvent should have been specified but the presence of a solvent in this reaction is taken as read. – Waylander Feb 2 at 15:40
• What would be the mechanism ..? π complex formation like in the case of Cl2 .. and should the solvent be non polar ..@waylander – Muskaan Feb 2 at 18:50
• Formation of an iodonium ion [3] intermediate. This reaction will occur in most solvents due to the presence of a very good internal nucleophile. – Waylander Feb 2 at 21:12