Rearrangement

I have a doubt in the last step of this question
No description
13 Replies
iTeachChem Helper
@Dexter
iTeachChem Helper
Note for OP
+solved @user1 @user2... to close the thread when your doubt is solved. Mention the users who helped you solve the doubt. This will be added to their stats.
Nimboi
NimboiOP5d ago
No description
Nimboi
NimboiOP5d ago
in this step when the H(+) dehydrates the alcohol group and leaves behind a carbocation why does it not rearrange to the more stable leftmost tertiary spot, where it would also form a six membered ring?
Opt
Opt5d ago
It doesn't?
Nimboi
NimboiOP5d ago
wha? i got the answer that way what happens
Opt
Opt5d ago
It's esterification. Alcohol dissociates, gives O(-), which attacks C=O
Nimboi
NimboiOP5d ago
oh wtf
Opt
Opt5d ago
-OH on C=O is not a particularly good leaving group, so the H(+) takes care of that
Nimboi
NimboiOP5d ago
i used the wrong formula and got the right answer how nice
Opt
Opt5d ago
Happens. You're screwed when one of the Oxygen just happens to be an ¹⁸O though.
Nimboi
NimboiOP5d ago
yeah that makes sense 💀 🔫 tvym tyvm* +solved Opt
iTeachChem Helper
Post locked and archived successfully!
Archived by
<@717724055217635398> (717724055217635398)
Time
<t:1737125702:R>
Solved by
<@763645886500175892> (763645886500175892)

Did you find this page helpful?