The intermediate A and the major product B formed in the following reaction are
F1 Savita Teaching 25-5-23 D48

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CSIR-UGC (NET) Chemical Science: Held on (15 Dec 2019)
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  1. F1 Savita Teaching 25-5-23 D49F1 Savita Teaching 25-5-23 D50
  2. F1 Savita Teaching 25-5-23 D51F1 Savita Teaching 25-5-23 D52
  3. F1 Savita Teaching 25-5-23 D53 F1 Savita Teaching 25-5-23 D54
  4. F1 Savita Teaching 25-5-23 D55F1 Savita Teaching 25-5-23 D56

Answer (Detailed Solution Below)

Option 2 : F1 Savita Teaching 25-5-23 D51F1 Savita Teaching 25-5-23 D52
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Detailed Solution

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Concept:-

The goes via cis hydrogenation followed by the electrocyclic reaction.

Lindlar catalyst:
5%Pd-CaCO3 + Pb(OCOCH3)2 + F1 Savita Teaching 25-5-23 D57
Function:

Cis hydrogenation of alkyne to form an alkene

Example:
F1 Savita Teaching 25-5-23 D58
Electrocyclic reaction:-

It involves ring opening and ring-closing by the formation or breaking of new \(\sigma \) bond from \(\pi\) bond through the concerted mechanism.

Points to remember:

  • Be it thermal/photochemical both are allowed reactions.
  • Under the thermal condition

[ 4n= conrotation, 4n+2= disrotation ]

  • Under the photochemical condition

[4n = disrotation, 4n + 2 = conrotation]

Example:
 F1 Savita Teaching 25-5-23 D59
Explanation:-

Here is the mechanism of the reaction;

  • The first step is cis-hydrogenation of alkyne followed by electrocyclic ring-closing.
    F1 Savita Teaching 25-5-23 D60

Conclusion:-

Therefore the intermediate A and the major product B formed in the following reaction are
F1 Savita Teaching 25-5-23 D51F1 Savita Teaching 25-5-23 D52

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