The structure of the reactive intermediate generated by reaction of CHCl3 and KOH is

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CSIR-UGC (NET) Chemical Science: Held on (16 Feb 2022)
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  1. F3 Vinanti Teaching 04.01.23 D18
  2. F3 Vinanti Teaching 04.01.23 D19
  3. F3 Vinanti Teaching 04.01.23 D20
  4. F3 Vinanti Teaching 04.01.23 D21

Answer (Detailed Solution Below)

Option 2 : F3 Vinanti Teaching 04.01.23 D19
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Detailed Solution

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Concept:

  • Carbenes are neutral species with two unshared valence electrons, that is, these species are electron deficient species.
  • Parent carbene, CH2, is also called methylene. These are short lived species.
  • Carbenes are of two types( classified on the basis of spin multiplicity): 1. singlet carbenes and 2. triplet carbenes
  • Singlet carbenes or fisher carbenes have their spin paired electrons. They are sp2 hybridised and acts as an electrophile
  • Triplet carbenes or schrock carbene have unpaired valence electrons and they are either sp2 or sp hybridised. They acts as nucleophile.

 

Explanation:

The reaction of CHCl3 with KOH gives carbene intermediate:

F3 Vinanti Teaching 04.01.23 D22

F3 Vinanti Teaching 04.01.23 D23

The resultant carbene is singlet because lone pair of Cl can be back donate in the empty p-orbital to stabilize it.The spin paired valence electrons stays in hybrid sp2 orbital.

Structure of generated singlet carbene is: 

F3 Vinanti Teaching 04.01.23 D24

Conclusion:

Hence, CHCl3 on reaction with KOH generates a singlet carbene, (:CCl2 ) whose structure is:

F3 Vinanti Teaching 04.01.23 D19

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