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Question : destroyer roadmap #3 (picture)

Discussion in 'DAT Discussions' started by I Brush My Teeth, Aug 3, 2015.

  1. I Brush My Teeth

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    Can someone tell me why these two reactions yield different products?

    I thought it was just a simple E2 where a double bond would be made at the most stable carbon
     

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  2. WTN13

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    What is the reaction?
     
  3. BeaverLover

    BeaverLover SDN Gold Donor
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    The reactant in the above reaction is a bulky base, forming a anti-Zaitzev rule...I think
     
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  4. orgoman22

    orgoman22 DAT DESTROYER
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    The are indeed BOTH E2 reactions. Look closely at the employed base. If C2H5O-/C2H5OH is used we do a Zaitsev elimination whereby the most substituted alkene is formed. In the reaction going at the top, a larger, sterically hindered base was used, We used Sodium t-Butoxide...this reagent gave E2 Hoffmann, whereby the less substituted alkene was formed. For further clarity, see the David Klein text book which gives many more examples of this VITAL reaction series.

    Hope this helps

    Dr. Jim Romano
     
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  5. ThunderSplash

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    A big base can't get to the "inner" H so it grabs the H the outside and makes less substituted alkene. A small base can grab the "inner H" and makes most substituted alkene. Look at the mechanism and it will make sense. It confused me too!
     
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  6. I Brush My Teeth

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    Appreciate it! After so much studying, the little things are falling out of my brain :( haha 2 weeks left!
     
  7. orgoman22

    orgoman22 DAT DESTROYER
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    When the little things fall out pick them up and put them back in!:)

    :DKeep going! The finish line is in sight!

    Nancy
     
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  8. ThunderSplash

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    I used my last week to take 2 full lengths and review Destroyer's Roadmaps (if you know these you're golden) and a sheet where I kept extra Biology stuff that was giving me trouble. You're in the home stretch! Stay focused.
     
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  9. WTN13

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    Woops, didn't see the attachement. They got it covered though!
     

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