The following transformation involves a series of

F2 Madhuri Teaching 10.01.2023 D33

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CSIR-UGC (NET) Chemical Science: Held on (26 Nov 2020)
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  1. electrocyclic ring-opening and closing reactions.
  2. cycloaddition and cycloreversion reactions.
  3. sigmatropic rearrangements.
  4. cheletropic addition and elimination reactions.

Answer (Detailed Solution Below)

Option 2 : cycloaddition and cycloreversion reactions.
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Concept:

Cycloaddition Reaction:

  • The cycloaddition reaction is a chemical reaction in which two or more unsaturated molecules combine with each other to form a cyclic compound, with a reduction of bond multiplicity.
  • In other words, cycloaddition reaction indicates the addition of two or more π-bonds to form a cyclic adduct with the formation of bonds at the end of the pi bonds.

Explanation: 

  • The reaction is a [4+2]π cycloaddition reaction followed by a cycloreversion reaction, in which 5-oxo-3-phenyl-4,5-dihydro-1,2,3-oxadiazol-3-ium-4-ide acts as a dipolarophile. whereas the (1Z,5Z)-cycloocta-1,5-diene acts as a dienophileThe dipolarophile reacts in a cycloaddition reaction with 1,3-dipoles.

F2 Madhuri Teaching 10.01.2023 D34

  • The reaction proceeds through the following mechanism

F2 Madhuri Teaching 10.01.2023 D35

Conclusion:

Hence, the following transformation involves a series of ​​cycloaddition and cycloreversion reactions.

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