The correct order of the reactions involved in the following transformation is
F3 Vinanti Teaching 29.05.23 D61

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CSIR-UGC (NET) Chemical Science: Held on (15 Dec 2019)
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  1. Michael addition, Quasi-Favorskii rearrangement, Aldol condensation
  2. Quasi-Favorskii rearrangement, Michael addition, Aldol condensation
  3. Michael addition, Aldol condensation, Quasi-Favorskii rearrangement
  4. Aldol condensation, Quasi-Favorskii rearrangement, Michael addition

Answer (Detailed Solution Below)

Option 3 : Michael addition, Aldol condensation, Quasi-Favorskii rearrangement
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Concept:

→ Michael addition involves the formation of a reactive intermediate, which can be either an enolate or an enamine, followed by its attack on the alpha,beta-unsaturated carbonyl compound.

The resulting product is often a beta-keto carbonyl compound, which can be further modified through various chemical reactions.

→ Aldol condensation involves the nucleophilic addition of an enolate ion to the carbonyl group of another carbonyl compound, followed by dehydration to form a double bond between the alpha and beta carbons of the resulting aldol product.

The reaction can be catalyzed by a variety of bases, including hydroxide, alkoxide, and amine bases.

→ The Quasi-Favorskii rearrangement involves the conversion of a beta-hydroxy ketone or aldehyde to an alpha, beta-unsaturated ketone or aldehyde through a base-catalyzed intramolecular rearrangement. It is called "quasi" because it is similar to the Favorskii rearrangement but occurs through a different mechanism.

The mechanism of the Quasi-Favorskii rearrangement involves the deprotonation of the beta-hydroxy group by a base, followed by intramolecular attack of the oxygen atom on the adjacent carbonyl group.

The resulting intermediate then undergoes a proton transfer and elimination of the leaving group, leading to the formation of the alpha, beta-unsaturated carbonyl compound.

Explanation: 
F3 Vinanti Teaching 29.05.23 D62

F3 Vinanti Teaching 29.05.23 D63
Conclusion:
The correct answer is option 3.

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