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Topic: Elimination  (Read 3026 times)

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Offline Dolphinsiu

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Elimination
« on: May 06, 2007, 04:00:35 AM »
The following is Fischer projection     

     Ph                   Ph
      l                      l
Br ----  H           Br -----  H            OH-
      l           ,          l                  ---->
H  ----  Ph         H  ----- Me
      l                      l
     Ph                   Ph

    (A)                  (B)

Which one is more reactive in elimination?

My guess is that B is more reactive as methyl group is electron-donating group which can stabilize the carbocation. Am I correct?

But someone say A is more reactive, as conjugated double bond is formed when Ph is attached, energy state become lower.

Which one is correct?

Offline Yggdrasil

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Re: Elimination
« Reply #1 on: May 06, 2007, 04:18:59 AM »
The second explanation clearly wrong because there is an sp3 carbon between the site of the carbocation and the Ph/Me.  Your first guess does make some sense.  However, what about E2 elimination?

Offline Dolphinsiu

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Re: Elimination
« Reply #2 on: May 06, 2007, 12:15:31 PM »
It is secondary halide! As strong base is used, E2 is favored.

But I still don't know when syn elimination is more favorable than anti-elimination, such as pyrolysis (syn elimination).

Do you know?

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