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.
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