Fundamentals of Organic ChemistryChemistryAldehydes and Ketones
Identify the major product of the following reaction: [ (ii) H₂O / H^+ ] (i) Excess MeMgCl Major Product
Correct answer
3
Step-by-step solution
The Grignard reagent ( MeMgCl ) acts as a strong base and first abstracts the acidic proton from the phenolic -OH group to form a phenoxide ion. Another equivalent of MeMgCl acts as a nucleophile and attacks the carbonyl carbon to form a magnesium alkoxide intermediate. The resulting -chloroalkoxide undergoes an intramolecular S_ N 2 reaction. The alkoxide oxygen displaces the chloride ion on the adjacent carbon, forming an epoxide ring. Since MeMgCl is present in excess, an additional equivalent attacks the less s