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Question

In the following conversion 

the major product [X] is

The correct answer is

The reaction given in the problem involves an enolate reacting with an organocopper reagent (Gilman reagent) and then further with an iodomethyl ester to produce the final product [X]. Let's break down the reaction steps:

  1. First, the lithium diorganocopper reagent, created from the reaction of an organolithium compound with copper(I) iodide, is highly effective for conjugate addition to α,β-unsaturated carbonyl compounds.
  2. The given organocopper reagent will undergo a 1,4- or conjugate addition with the unsaturated carbonyl compound present in the initial substrate.
  3. The product of this addition will have the organo group attached to the β-position of the carbonyl compound, while the α,β-unsaturation is eliminated.
  4. Next, the reaction proceeds with the vinyl iodide and methyl ester compound in the presence of HMPA, facilitating a coupling reaction that extends the carbon chain by adding the vinyl group to the β-carbon as introduced in the previous step.

Following these steps, of the options given, the major product [X] is:

This option correctly represents the structure wherein the organocopper addition has occurred at the β-position followed by successful coupling at the α-position, resulting in the final compound depicted.

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Important Questions from Organic Transformations

  1. The major products X and Y in the following reaction sequence are 

  2. The following conversion is an example of 

  3. The major product formed in the reaction given below is

  4. In the following reaction 

    the major product [X] is

  5. In the following reaction 

    the major product [X] is

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