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Fundamentals of Organic ChemistryChemistryAldehydes and Ketones

Aldehydes and ketones react with -bromo esters and zinc metal in an ether or benzene medium to yield:

Options

  1. A-keto acids
  2. B-hydroxy esters
  3. C-keto esters
  4. D-keto esters

Correct answer

B. -hydroxy esters

Step-by-step solution

The reaction of aldehydes or ketones with -bromo esters and zinc metal in an ether or benzene medium is known as the Reformatsky reaction. Zinc reacts with the -bromo ester to form an organozinc intermediate, which is a zinc enolate. This intermediate acts as a nucleophile and attacks the carbonyl carbon of the aldehyde or ketone to form a zinc alkoxide. Upon acidic hydrolysis, the zinc alkoxide yields a -hydroxy ester. The general reaction is: R₂C=O + Br-CH₂-COOR' + Zn ether R₂C(OZnBr)-CH₂-COOR' R₂C(OZnBr)-CH₂-COO

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