Elimination with Amines

Asked Nov 26 '15 at 14:24

Active Nov 26 '15 at 14:24

Viewed 53 times

$\hspace{35 mm}$

ATTEMPT:

Since $\ce{Et3N}$ is a weak base and the carbon to which $\ce{Br}$ is attached is tertiary, we can rule out $\mathrm{E2}$ and $\mathrm{S_N2}.$ As we are providing heat, the reaction is likely to go via $\mathrm{E1}$ forming a stable tertiary carbocation.

Now as the base is bulky it will knock out the most easily available $\ce{H}$, giving us the less substituted alkene.

However my text suggests that this reaction proceed via $\mathrm{E2}$ with the base taking a $\ce{H+}$ and knocking off $\mathrm{Br}$ to give the same final product.

In general with amines out of $\mathrm{E1}$ and $\mathrm{E2}$ which reaction is preferred if there is a possibility of stable carbocation formation?

asked Nov 26 '15 at 14:24

miyagi_do

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Didn't you post this a couple of days ago? Why did you delete the first question and repost it? – bon Nov 26 '15 at 14:45
@bon , The question was not getting enough attention.So i repost it. – miyagi_do Nov 26 '15 at 14:55
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@yasir You should not repost your question if it is not getting enough attention. Instead, use a bounty. – wythagoras Nov 26 '15 at 15:49
@wythagoras, I tried using a bounty on this.HereBut nothing happened. – miyagi_do Nov 26 '15 at 22:32

Elimination with Amines

ATTEMPT:

0 Answers0