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
- A-keto acids
- B-hydroxy esters
- C-keto esters
- 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