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Topic: Is my explanation of why I get the exo product correct here?  (Read 890 times)

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Offline yourdeath01

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Is my explanation of why I get the exo product correct here?
« on: October 17, 2019, 12:28:18 PM »
Basically we did a diels-alder lab where we reacted maleic anhydride and furan, measure melting point and decide from melting point using literature melting point if the product is endo or exo and therefore if its under kinetic or themodynamic control.

Heres the overall reaction:

https://prnt.sc/pjd50y

Anyways its asking me to identify of my product is endo or exo. This one is easy because I can compare the melting point to the literature melting point and so I know I get the exo product.

But then it asks me a weird question

"Propose an explanation for the stereo chemistry of your product"

Here is how I answered that question above, let me know if its correct guys! Basically its asking me why do I get the exo vs. The endo product.

Here are my diagrams:

Endo adduct: https://imgur.com/ameyWft
Exo adduct + TS state for both: https://imgur.com/DdmRjIV
In endo addition maximum accumulation of of double bond takes place.

The addition process, the transition state involves the secondary orbital overlap of nonbonding atoms.

In exo addition no secondary orbital overlap is present.

Thus endo addition follows a lower energy pathway results in formation of kinetically controlled endo-adduct readily as major product.

However exo-adduct is thermodynamically more stable so after some time there will be an equilibrium mixture of both exo and endo adduct.

This is what I got to answer the question

Propose an explanation for the stereo chemistry of your product

Is this all good you think or should I make adjustments?

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