The correct relationship between the two faces of the C=O group in compounds A and B is

F1 Madhuri Teaching 16.02.2023 D3

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CSIR-UGC (NET) Chemical Science: Held on (16 Feb 2022)
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  1. A = diastereotopic; B = enantiotopic
  2. A = B = enantiotopic
  3. A = enantiotopic; B = diastereotopic
  4. A = B = diastereotopic

Answer (Detailed Solution Below)

Option 1 : A = diastereotopic; B = enantiotopic
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Detailed Solution

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Concept:

Enantiomers : 

  • Enantiomers  are a pair of molecules that exist in two forms that are mirror images of one another but cannot be superimposed one upon the other.
  • Have identical physical properties except for the ability to rotate plane-polarised light.

Diastereomers : 

  • Diastereomers are defined as compounds with the same molecular formula and sequence of bonded elements but are non-superimposable non-mirror images.
  • They have distinct physical properties. Diastereomers are stereoisomers with two or more chiral centers that are not enantiomers.
  • Enantiomers and diastereomers are the only two stereochemical relationships that you can have between any two molecules.

The stereoisomers are any two molecules that fulfill the following two requirements: Both molecules must have the same molecular formula, and. Both molecules must have the same atom connectivity.

Explanation:

This structure A is having sp3 hybridized carbon on which oxygen is present due to which it can rotate thus it is diastereotopic in structure B there is a plane passing through the centre of the bridge and it will produce a non-superimposable mirror image thus it is enantiotopic

Conclusion: option A is correct.

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