MolSynapsequestion bank
MolSynapse / Question bank / Reduction, Oxidation and Hydrolysis in Organic Chemistry / Hydrolysis of esters, amides, nitriles and halides
JEE Advanced levelSingle correct optionDifficulty 3 of 3ro158

Methyl 5,5-dimethoxypentanoate, , is heated with aqueous NaOH. After cooling, the mixture is treated with warm dilute in excess water. The main organic product is

  1. A5-oxopentanoic acid,
  2. Bpentanedioic acid
  3. C5,5-dimethoxypentanoic acid
  4. Dmethyl 5-oxopentanoate

Answer: A

Hot aqueous NaOH saponifies the ester to the carboxylate while the acetal is stable to base. Dilute aqueous acid then hydrolyses the acetal to the aldehyde (with 2 ) and protonates the carboxylate. The product is the aldehyde-acid .
Practice Reduction, Oxidation and Hydrolysis in Organic Chemistry More on Hydrolysis of esters, amides, nitriles and halides
Previous questionNext question

More questions on Hydrolysis of esters, amides, nitriles and halides