Question
Download Solution PDFThe major products A and B formed in the following transformations are
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CSIR-UGC (NET) Chemical Science: Held on (26 Nov 2020)
Answer (Detailed Solution Below)
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Download Solution PDFConcept:
- According to HSAB principle, both thermodynamically and kinetically hard acids prefer hard bases and soft acids soft bases. Specifically, thermodynamically, hard acids form stronger acid-base complexes with hard bases while soft acids form stronger complexes with soft bases.
- For a \(\alpha,\beta\)-unsaturated carbonyl compound, the \(\alpha\)-c atom act as a soft electrophile, and the \(\beta\)-c atom act as a hard electrophile.
Explanation:
- The reaction pathway is shown below:
- From the above reaction, we can see that in presence of NaH (strong base), the amine group (-NH2 group) undergoes deprotonation and forms a hard nucleophilic center (N atom). Thus, it will attack the hard electrophile according to the SHAB principle and forms the major product A.
- In presence of NaH (strong base), the thiol group (-SH group) undergoes deprotonation and the S atom being a soft nucleophilic center will attack the softer electrophile according to the SHAB principle. This reaction leads to the formation of compound B as the major product.
Conclusion:
The major products A and B formed in the following transformations are
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