Amines/Elimination
After MeI makes N(Me)3+, shouldn't there be E1cb reaction to form (3)?
Answer:(2)
11 Replies
@Dexter
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.Oh, a Hoffman elimination been a while since I saw this.
Yeah, but the answer key says it should be saytzeff product.
Would there be E2 or something instead of E1cb?
E1cB gives you (2) here doesn't it?
Abstract proton from beta carbon, you get a resonance stabilised carbanion, electron pairs shifts to pi bonding orbitals, kicks out the NMe3
Ah.
But doesn't the steric hindrance makes the base abstract proton from the right-most carbon?
Trimethyl nitrogen is much more of a steric hindrance than a phenyl group
Ah.
So whenever there is a N(Me)3 group attached to carbon chain, we abstract proton from the most stable carbocation location or looking at steric hindrance?
(In general cases)
Carbanion, but yes
Especially with a bulky basr
*base
I see. Carbanion stability>steric hindrance..
+solved @Opt
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