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Question

The major product formed in the following reaction is

The correct answer is

Step-by-step Solution:

The given reaction involves a compound undergoing reduction with Samarium(II) iodide (SmI2) in tetrahydrofuran (THF), followed by methanol (MeOH) treatment. This is a typical reaction setup for a reductive coupling or pinacol-type reaction.

Explanation:

  1. Reagent Action: SmI2 is a one-electron reducing agent, primarily used to reduce carbonyl groups and facilitate coupling reactions. It can induce radical formation from α,β-unsaturated esters or carbonyl compounds.
  2. Reaction Process: The α,β-unsaturated ester in the compound is a potential site for reduction. SmI2 will first convert into an organosamarium species that can undergo radical addition to the carbonyl carbon.
  3. Product Formation: The radical formed can then couple with another equivalent, typically resulting in a dimerization or a cyclization product, followed by quenching with methanol to give a stable alcohol product.

Correct Option Identification:

The product shown in this option represents the expected outcome of this reaction sequence: reduction and coupling at the reactive sites to form a more complex structure, ultimately stabilized and capped by methanol as a hydroxyl group is introduced.

Conclusion: Given the reagents and the substrate, the major product formed involves the reduction of the ester bond with subsequent coupling of radicals, resulting in the depicted structure.

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  5. The major product formed in the following reaction is

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