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Author Topic: diels alder reaction with maleic anhydride  (Read 210 times)

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mana

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diels alder reaction with maleic anhydride
« on: April 15, 2018, 08:42:04 AM »

hi all
 which one ( A, B or C) react faster respectively with maleic anhydride ?
I know steric effect is dominant here but I can't understand why C is the fastest and then A and B ???
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Enthalpy

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Re: diels alder reaction with maleic anhydride
« Reply #1 on: April 16, 2018, 05:21:49 AM »

A drawing on a flat papersheet or screen does not represent all the shapes a molecule can take.
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wildfyr

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Re: diels alder reaction with maleic anhydride
« Reply #2 on: April 16, 2018, 07:30:35 AM »

Think about other forms A and B can take that C cannot.
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mana

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Re: diels alder reaction with maleic anhydride
« Reply #3 on: April 16, 2018, 09:31:31 AM »

yes that's right  :D
2,3-ditersiobutyl 1,3-butadiene (B) is not s-cis as mentioned in the figure and it must be s-trans because of steric hindered  so it doesn't react with maleic anhydride but what about A?
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wildfyr

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Re: diels alder reaction with maleic anhydride
« Reply #4 on: April 16, 2018, 10:25:10 AM »

The question is about reaction speed, they can all react to one degree or another.

Both A and B can be cis or trans, however, which form do you think they prefer? And can they interconvert?

Is C cis or trans? Can it interconvert?
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