The major product formed in the following reaction sequence is

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CSIR-UGC (NET) Chemical Science: Held on (26 Nov 2020)
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Seating Arrangement
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Concept:

Wittig reaction:

  • In the Wittig reaction, an aldehyde or a ketone is reacted with a triphenyl phosphonium ylide to yield an alkene along with triphenylphosphine oxide.
  • An example is shown below:

Claisen rearrangement:

  • In a claisen rearrangement reaction, the allyl vinyl ether is converted into a gamma, delta-unsaturated carbonyl compound on heating or in presence of a Lewis acid.
  • An example is shown below:

Cope rearrangement:

  • The Cope rearrangement is a chemical reaction in organic chemistry that involves the [3,3]-sigmatropic rearrangement of 1,5-dienes on heating.
  • An example is shown below:

Trans Esterification reaction:

  • The transesterification reaction is the process of exchanging the organic functional group R1 of an ester with the organic group R2 of an alcohol. These reactions are often catalyzed by the addition of an acid or base catalyst.

Explanation:

  • The reaction pathway is shown below:

  • From the above reaction, we can see that the phosphonium ylide reacts with the aldehyde to form the alkene.
  • In the next step, the generated alkene undergoes a [3,3] Claisen rearrangement reaction followed by a [3,3] Cope rearrangement reaction.
  • In the next step, the intermediate product undergoes an [1,5] H shift followed by a transesterification reaction to give the final product.

Conclusion:

Hence, the major product formed in the following reaction sequence is 

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