3
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$\hspace{35 mm}$Reaction

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?

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4
  • 1
    $\begingroup$ Didn't you post this a couple of days ago? Why did you delete the first question and repost it? $\endgroup$
    – bon
    Commented Nov 26, 2015 at 14:45
  • $\begingroup$ @bon , The question was not getting enough attention.So i repost it. $\endgroup$
    – miyagi_do
    Commented Nov 26, 2015 at 14:55
  • 1
    $\begingroup$ @yasir You should not repost your question if it is not getting enough attention. Instead, use a bounty. $\endgroup$
    – wythagoras
    Commented Nov 26, 2015 at 15:49
  • $\begingroup$ @wythagoras, I tried using a bounty on this.HereBut nothing happened. $\endgroup$
    – miyagi_do
    Commented Nov 26, 2015 at 22:32

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