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Question

The major product formed in the following reaction sequence is

The correct answer is

The given reaction sequence involves three main steps:

  1. The starting material is treated with LDA (Lithium diisopropylamide) at -78°C. LDA is a strong, non-nucleophilic base, which abstracts the most acidic hydrogen in the compound. In this case, the hydrogen at the alpha position to the carbonyl group is abstracted, forming an enolate ion.
  2. Next, the enolate ion is treated with PhSeCl (Phenylselenyl chloride). The enolate acts as a nucleophile and attacks the electrophilic phenylselenium, leading to the formation of a selenoether.
  3. Finally, the selenoether is oxidized using hydrogen peroxide (H2O2). This step involves the conversion of the selenide to a selenoxide, followed by elimination to form the corresponding alkene.

The combined reaction steps result in an overall process of α-selenation followed by elimination, leading to the formation of an α,β-unsaturated ketone, which is the major product of the reaction sequence. This transformation is known as the “Julia-Lythgoe olefination.”

The correct structure of the major product, considering the reaction mechanism described, is

This product exhibits a double bond between the α and β positions relative to the original carbonyl group, making it an α,β-unsaturated ketone.

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Important Questions from Organic Transformations and Reagents

  1. The presence of unsaturation in an organic compound can be detected by

  2. Which of the following boron compounds is used as a reducing agent in organic synthesis?

  3. In elimination reaction of sec-Butyl trimethylammonium hydroxide, major product formed would be ________.

  4. Find out the suitable products in the following Grignard reaction:

     

  5. What will be the product in the following reaction ?

     

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