3
$\begingroup$

I am asked to determine whether the following process is likely to involve a carbocation rearrangement or not:

impossible rearrangement

I think it is possible through the rearrangement given above (though the rearrangement cannot become a secondary or primary carbocation). Can someone please clarify if the carbocation rearrangement specifies a change in degree?

$\endgroup$
  • 2
    $\begingroup$ I feel your wording is a bit unclear. Do you mean to ask that whether this rearrangement is possible and whether it will be called a carbocation rearrangement even though there is no change in the degree of the carbocation? $\endgroup$ – Binary Geek May 15 '15 at 4:46
  • 1
    $\begingroup$ How do you say the rearrangement cannot become a secondary or primary carbocation? And as Binary Geek there is no change inthe degree of the carbocation provide sime clarity. By what reference your thinking it is possible ? $\endgroup$ – Λjάγ Laggani May 15 '15 at 5:25
  • 1
    $\begingroup$ What I get of your question, the process you have made is not possible. It will help if you c;arify. $\endgroup$ – Rajat Jain May 15 '15 at 7:36
  • 1
    $\begingroup$ Try to draw the mechanism for the second transformation and you'll have your answer. $\endgroup$ – jerepierre May 15 '15 at 15:08
  • 1
    $\begingroup$ @jerepierre That's why I added ~ ? to the arrow when I replaced the drawing ;-) $\endgroup$ – Klaus-Dieter Warzecha May 19 '15 at 7:38
5
$\begingroup$

The most common carbocation rearrangements involve [1,2] hydride or alkyl shifts. As a typical result a secondary carbocation is converted to a more stabilized tertiary carbocation.

In the course of these reactions, the migrating group and the positive charge change place, they move to opposite directions.

This is not the case in your example.

I fail to see how your transformation can be described as a cationic rearrangement!

$\endgroup$
  • 1
    $\begingroup$ Looks like the OP added some info in the comments after you answered the question. It would be good if you do so :) $\endgroup$ – Del Pate May 19 '15 at 6:01

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.