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Question 47

Find out the major product from the following reaction.

Step 1: Conjugate Addition (1,4-addition)

  • The combination of MeMgBr and CuI forms a Gilman reagent (organocopper species), which selectively undergoes 1,4-addition (conjugate addition) rather than 1,2-addition.
  • The methyl group $$(\text{Me}^{-})$$ attacks the $$\beta$$-carbon of the 3-methylcyclohex-2-en-1-one.
  • This creates a quaternary center at the 3-position and generates a nucleophilic enolate intermediate.

Step 2: Alpha-Alkylation

  • Instead of quenching with water, the reaction adds n-PrI (n-propyl iodide).
  • The enolate oxygen-carbon double bond reforms, and the $$\alpha $$-carbon acts as a nucleophile to attack the n-propyl iodide via an $$S_{N}2$$mechanism.
  • The n-propyl group is added to the 2-position (the $$\alpha $$-carbon).
Screenshot 2026-05-25 172642

The major product of this reaction sequence is 3,3-dimethyl-2-propylcyclohexanone.

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