4
$\begingroup$

This question already has an answer here:

I have read that halogens have a stonger -I (inductive effect) than +M (mesomeric effect),then why do they stabilise a carbocation instead of destabilising it?

I asked this doubt to my teacher and he said that halogens like fluorine do not exert -I on a carbocation and hence they stabilise a carbocation through +M,is this true?

$\endgroup$

marked as duplicate by Mithoron, airhuff, pentavalentcarbon, Todd Minehardt, andselisk Jan 16 '18 at 23:22

This question has been asked before and already has an answer. If those answers do not fully address your question, please ask a new question.

1
$\begingroup$

Fluorine belongs to the same period as Carbon. Carboncation is electron deficient which has its two $2p$ orbitals vacant. One electron of carbon in $2p$ goes into the formation of $\ce{C-F}$ $\sigma$ bond. $\ce{F}$ has $2p$ orbital containing a lone pair which can be donated to the $2p$ vacant orbitals of carbocation. Same size $2p$ orbitals of Carbon and Fluorine overlap effectively to form a $\pi$ bond.

$\endgroup$
-1
$\begingroup$

Carbocations are stabilized by neighboring atoms with lone pairs. The key stabilizing influence is that the neighboring atom can donate a pair of electrons to the electron-poor carbocation. In this way halogenes, nitrogen or oxygen can actually be an electron-donor group and stabilize the carbocation.

$\endgroup$
  • $\begingroup$ This is stated in the question. The actual question is about why the inductive effect does not dominate the mesomeric effect in carbocations, whereas it usually does for fluorine. $\endgroup$ – bon Jan 14 '16 at 19:12
-1
$\begingroup$

Most of the times the question that comes in the examinations is that why CH2F+ is more stable than CH2Br+ or CH2I+. The reason behind it is that the p orbital of fluorine overlaps more effectively than that of Br or I with the carbon atom and therefore disperses the charge on it. refer to K L Chugh for the details.

$\endgroup$

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