1
$\begingroup$

enter image description here

In the image, what would happen after step 2?

  1. Will a double bond be formed between carbon 3 and 4? If this is the case, then we would get benzene in the end.
  2. But, if the positive charge in shifted to carbon 1, then won't it be a more stable carbocation?
  3. Also, if a double bond were to be formed between carbon 1 and 4 now, it would be more substituted than a double bond between carbon 3 and 4.

In spite of all these factors, the double bond is formed between carbons 3 and 4, and benzene is formed.

Kindly explain how this process takes place.And, please tell me how to name this compound.

$\endgroup$
  • $\begingroup$ I'm suspicious of making a primary carbocation. It's possible that you would get a concerted shift, but even next to a cyclopropane, that looks bad... $\endgroup$ – Zhe Oct 19 '16 at 15:06
1
$\begingroup$

The following takes place- not available

And then H3O+ can be assumed to give H+ and H2O. Try it out and you'll get to the product.

If the positive charge is shifted to carbon 1, it would form a more stable alkene since it is more substituted. But after formation of C1-C4 double bond, no further reaction will occur since after expansion + charge will be on a double bonded carbon which would be highly unstable. Since Benzene is more stable than the product which will be formed after shifting of + charge to Carbon 1, and since heat is also applied, there will be enough energy to form more stable benzene and thus the reaction takes place in such a manner.

$\endgroup$

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

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