Chemistry - STEREO ISOMERISM Question with Solution | TestHub
ChemistrySTEREO ISOMERISMABSOLUTE AND RELATIVE CONFIGURATIONEasy2 minQB
ChemistryEasysingle choice
This compound racemizes in base. Why is that ?
ethyl (S)-2-hydroxypropanoate (ethyl lactate)
Options:
Answer:
A
Solution:
Ans. Base removes the acidic alpha-H on the stereocentre (the carbon between OH and C=O), giving a planar, achiral enolate; reprotonation from either face regenerates both enantiomers equally, so the compound racemizes.
Sol. The stereocentre of ethyl lactate is alpha to the ester carbonyl and bears one H. Hydroxide deprotonates it to a flat enolate in which the former stereocentre is sp2 and achiral; work-up reprotonates it from either face with equal probability, giving a racemic mixture.
Stream:JEESubject:ChemistryTopic:STEREO ISOMERISMSubtopic:ABSOLUTE AND RELATIVE CONFIGURATION
⏱ 2mℹ️ Source: QB
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