I want to do Wurtz reaction of 1-bromo-3-chlorocyclobutane:


Wikipedia suggests to do an intramolecular reaction. Instead, I remember reading somewhere that bromine is more reactive and hence we should do an intermolecular reaction, and attach two carbons to where $\ce{Br}$ was attached.

So, what product is formed in the Wurtz reaction of 1-bromo-3-chlorocyclobutane?

  • $\begingroup$ Cyclobutane is not planar, it has butterfly like structure. Intra molecular reaction is more possible $\endgroup$
    – Harish BA
    Dec 2, 2019 at 4:18

1 Answer 1


Br is a much better leaving group than Cl.First of all presuming that Cyclobutane is stabilized by substitutent groups is important since it wil gradually rearrange itself to buta diene.But since it is a theoretical question hence we can say that it should add to the Br side since Br leaves more efficiently being larger in size than Cl and hence having less efficient orbital overlap with Carbon as well as a large electronic repulsion due to the large number of electrons it has is the reason behind this.And the major product will probably be a bicyclo [1.1.0] butane since it is the kinetic product. so basically your answer- enter image description here

  • 1
    $\begingroup$ I am not sure about this. Chlorine has a higher electron affinity/ electronegativity compared with bromine and should be reduced first. Then you could have an nucleophilic attack at the C-Br bond. This will result in an asymmetric minor product. $\endgroup$ May 13, 2014 at 6:31

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service and acknowledge that you have read and understand our privacy policy and code of conduct.

Not the answer you're looking for? Browse other questions tagged or ask your own question.