Challenge Problem 17.73 X Incorrect. what is known as conjugated T-system? Ident

Question

Challenge Problem 17.73 X Incorrect. what is known as conjugated T-system? Identify the stability of the terminal and the internal furans. During a recent investigation into the chemistry of oligofurans (polymers of the furan heterocycle, which show potential to be used in materials), the investigators observed an interesting reaction with dienophiles. When trifuran (below) is treated with maleimide, only the terminal furan participates in a [4+2] reaction (Org. Lett. 2012, 14, 502-505) HN Exclusive product Not observed Choose the reasonable explanation for the above observation. Select all that apply. If the terminal furan reacts, the product is still conjugated there are two furans that share resonance stabilization. IV If the internal furan were to react, the conjugation would be broken, leaving behind two isolated furans. This molecule would be much higher in energy because of the loss of conjugation. If the internal furan reacts, the product is still conjugated there are two furans that share resonance stabilization. IV If the terminal furan were to react, the conjugation would be broken, leaving behind two isolated furans. This molecule would be much higher in energy because of the loss of conjugation. r Since the product distribution of a Diels-Alder reaction is determined by thermodynamic considerations, the higher energy product is not obtained. Question Attempts: 10 of 15 used

Explanation / Answer

Option 1,2,5 are correct, applicable explanation

remining 4,5 are incorrect they are not applicable.

If the termminal furan reacts, the product is still conjucate-there are two furans that shares the resonance stabilization. (Correct)

If the internal furan reacts , the conjucation would be broken, leaving behind two isolated furans. this molecule would be much higher in energy because the loss of conjugation (correct)

If the internal furan reacts, the product is still conjucated-there are two furans that shares the resonance stabilization. (Incorrect).

If the terminal furan reacts , the conjucation would be broken, leaving behind two isolated furans. this molecule would be much higher in energy because the loss of conjugation (Incorrect)

Since the product distribution of a diels alder reaction is determined by thermodynamic consideration, the higher energy product is not obtained. ( Correct)

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