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Topic: Migratory aptitude  (Read 8135 times)

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Offline orgoclear

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Migratory aptitude
« on: September 25, 2009, 11:37:09 PM »
What is the order of migratory aptitude?

In Wiki, it is given Ph>Tert>Secondary>Primary>Methyl>Hydride

While our textbook mentions

Hydride>Ph>Tert>Secondary>Primary>Methyl

Offline nj_bartel

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Re: Migratory aptitude
« Reply #1 on: September 26, 2009, 11:53:03 AM »
I was under the impression hydride was at the top of the list.  Definitely isn't at the bottom.

Offline a student

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Re: Migratory aptitude
« Reply #2 on: October 02, 2009, 12:11:06 PM »
that's my question too, is there any logical reason for this order, I mean does anyone know that what properties are necessary for a good immigrant group? ??? ???

Offline KritikalMass

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Re: Migratory aptitude
« Reply #3 on: October 05, 2009, 01:08:53 AM »
As with most everything in Ochem it has to do with stability and energy conservation.

What takes more energy- moving around a single puny Hydrogen atom, or moving around a whole Methyl group?

And why is it easier to move a Ph group than a tertiary carbon? Because of resonance the Ph group is stabilized. Yes it is bigger than a tertiary carbon, but since it has resonance it is lower in energy.

Why is it easier to move a tertiary carbon than secondary carbon? Because a tertiary carbon is more stable (lower in energy) than a secondary carbon.

Same reasoning applies to the rest of the question.

With Ochem always ask- What is stable? What is energy efficient?

Offline nj_bartel

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Re: Migratory aptitude
« Reply #4 on: October 05, 2009, 01:36:43 AM »
Tert > Sec > Methyl doesn't make sense, we're talking anions.

Offline exploring gul

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Re: Migratory aptitude
« Reply #5 on: October 24, 2009, 11:02:34 PM »
i have read that the group that carry more negative  charge ,will migrate because of electrostatic force of attraction energy will lower down.i agree with all this but i can t understand why the hydride has the greatest ability to migrate .in some books ph has greater migratory aptitude

Offline jinclean

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Re: Migratory aptitude
« Reply #6 on: October 25, 2009, 07:33:41 AM »
But in the Wolff's rearrangement the H is the top and other groups have the reverse direction

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