Chemistry · Covalent bond fission: Homolytic and heterolytic, free radicals, carbocations and carbanions, stability of carbocations and free radicals, electrophiles and nucleophiles

Assertion If a pure enantiomer of the following ester is hydrolysed in dilute al

Assertion If a pure enantiomer of the following ester is hydrolysed in dilute alkaline medium, a pure enantiomer of alcohol is obtained. Reason Under the given condition of hydrolysis, acyl oxygen heterolysis always takes place.

  • A. Both Assertion and Reason are correct and Reason is the correct explanation for Assertion
  • B. Both Assertion and Reason are correct but Reason is not the correct explanation for Assertion
  • C. Assertion is correct but Reason is incorrect
  • D. Assertion is incorrect but Reason is correct

Step-by-step solution

In alkaline hydrolysis of esters, the mechanism involves acyl-oxygen cleavage, where the bond between the carbonyl carbon and the alkoxy oxygen breaks. This leaves the chiral carbon of the alcohol part unaffected, preserving its configuration. Therefore, starting from a pure enantiomer of the ester yields a pure enantiomer of the alcohol. The Reason correctly describes the occurrence of acyl-oxygen heterolysis, which ensures no bond breaking at the chiral center, explaining the Assertion.
Practise more in this unitView MCQsSign up for full question bank