Problem: Indicate whether the compounds below undergo racemization when treated with aqueous acid or base. 

FREE Expert Solution

We are asked to identify whether the compounds below undergo racemization when treated with aqueous acid or base.

  • The acidic hydrogen atom present on alpha-carbon atom of carbonyl compounds can be removed in presence of an acid or a base to form enol. 
  • The alpha carbon needs to have hydrogen and should be a chiral center.


Compound A

  • Alpha hydrogen present
  • 4 different groups on the alpha carbon. 


Yes, the compound can undergo racemization when treated with aqueous acid or base.


Compound B

  • Alpha hydrogen present
  • However, there are 2 hydrogens in the alpha carbon meaning it is not chiral. 


The compound can't go under racemization


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Problem Details

Indicate whether the compounds below undergo racemization when treated with aqueous acid or base.

 

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What scientific concept do you need to know in order to solve this problem?

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