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Question:

The correct sequences of reagents for the following conversation will be:

[Ag(NH3)2]+OH−,H+/CH3OH,CH3MgBr

CH3MgBr,H+/CH3OH,[Ag(NH3)2]+OH−

CH3MgBr,[Ag(NH3)2]+OH−,H+/CH3OH

[Ag(NH3)2]+OH−,CH3MgBr,H+/CH3OH

Solution:

Tollens reagent oxidizes aldehyde to carboxylate ion. The carboxylate ion is then undergoes esterification reaction to form the corresponding ester. This ester, when reacted with Grignard's reagent, undergoes nucleophilic addition reaction to form the given product. Option D represents the correct sequence of the reagent.