In the following transformation, the enantiomerically pure lactone A provides

F2 Madhuri Teaching 27.03.2023 D123

This question was previously asked in
CSIR-UGC (NET) Chemical Science: Held on (26 Nov 2020)
View all CSIR NET Papers >
  1. equimolar amounts of syn- and anti-diastereomers of B, both of which are racemic
  2. equimolar amounts of syn- and anti-diastereomers of B, both of which are enantiomerically pure
  3. only syn-diastereomer of B, which is racemic
  4. only anti-diastereomer of B, which is enantiomerically pure

Answer (Detailed Solution Below)

Option 3 : only syn-diastereomer of B, which is racemic
Free
Seating Arrangement
3.4 K Users
10 Questions 20 Marks 15 Mins

Detailed Solution

Download Solution PDF

Concept:

​Activation of allylic electrophiles by palladium(0):

  • Allylic compounds with a good leaving group can form a π-allyl cation complex of palladium (0) via nucleophilic displacement reaction with controlled stereochemistry and regiochemistry.
  • The π-allyl cation complex gives the product upon attack by a nucleophile.
  • An example is shown below:

F2 Madhuri Teaching 27.03.2023 D124

  • The reaction usually proceeds with the retention of configuration at the reacting center.

Explanation:

  • The reaction pathway is shown below:

F2 Madhuri Teaching 27.03.2023 D125

  • From the above reaction, we can see that the reaction proceeds with the retention of configuration at the reacting center. It also suggests a double
    inversion.
  • The Coordination of Pd occurs to the double bond of the allylic lactone A on the less hindered face opposite to the leaving group. Also, we may think of the oxidative addition step as an invertive nucleophilic displacement of the leaving group by a pair of Pd electrons.
  • In the last step, the nucleophile then adds to the face of the π-allyl Pd cation complex opposite of the Pd metal.
  • This results in the formation of a syn-diastereomer B, which is racemic.

Conclusion:

Hence, In the following transformation, the enantiomerically pure lactone A provides only syn-diastereomer of B, which is racemic.

Latest CSIR NET Updates

Last updated on Jun 5, 2025

-> The NTA has released the CSIR NET 2025 Notification for the June session.

-> The CSIR NET Application Form 2025 can be submitted online by 23rd June 2025

-> The CSIR UGC NET is conducted in five subjects -Chemical Sciences, Earth Sciences, Life Sciences, Mathematical Sciences, and Physical Sciences. 

-> Postgraduates in the relevant streams can apply for this exam.

-> Candidates must download and practice questions from the CSIR NET Previous year papers. Attempting the CSIR NET mock tests are also very helpful in preparation.

Get Free Access Now
Hot Links: teen patti tiger teen patti master 51 bonus online teen patti