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Haloalkanes And Haloarenes

Question
CBSEENCH12010772

Arrange the carbanions left parenthesis CH subscript 3 right parenthesis subscript 3 comma space straight C subscript 6 straight H subscript 5 straight C with minus on top straight H subscript 2 space comma thin space straight C with minus on top Cl subscript 3 comma space left parenthesis CH subscript 3 right parenthesis subscript 2 space straight C with minus on top straight H  in order of their decreasing stability 

  • straight C subscript 6 straight H subscript 5 straight C with minus on top straight H subscript 2 space greater than space straight C with minus on top Cl subscript 3 space greater than thin space left parenthesis CH subscript 3 right parenthesis subscript 3 straight C with minus on top space greater than thin space left parenthesis CH subscript 3 right parenthesis subscript 2 straight C with minus on top straight H
  • thin space left parenthesis CH subscript 3 right parenthesis subscript 2 straight C with minus on top straight H greater than space straight C with minus on top Cl subscript 3 space greater than straight C subscript 6 straight H subscript 5 straight C with minus on top straight H subscript 2 greater than thin space left parenthesis CH subscript 3 right parenthesis subscript 3 straight C with minus on top space
  • space straight C with minus on top Cl subscript 3 space greater than straight C subscript 6 straight H subscript 5 straight C with minus on top straight H subscript 2 greater than thin space left parenthesis CH subscript 3 right parenthesis subscript 2 straight C with minus on top straight H greater than thin space left parenthesis CH subscript 3 right parenthesis subscript 3 straight C with minus on top space
  • thin space left parenthesis CH subscript 3 right parenthesis subscript 2 straight C with minus on top straight H greater than thin space left parenthesis CH subscript 3 right parenthesis subscript 3 straight C with minus on top space greater than space straight C with minus on top Cl subscript 3 space greater than straight C subscript 6 straight H subscript 5 straight C with minus on top straight H subscript 2

Solution

C.

space straight C with minus on top Cl subscript 3 space greater than straight C subscript 6 straight H subscript 5 straight C with minus on top straight H subscript 2 greater than thin space left parenthesis CH subscript 3 right parenthesis subscript 2 straight C with minus on top straight H greater than thin space left parenthesis CH subscript 3 right parenthesis subscript 3 straight C with minus on top space

Due to the –I effect of three chlorine atoms and due to pπ - dπ bonding CCl3 is extra stable.Carbanion follow stability order  space straight C with minus on top Cl subscript 3 space greater than straight C subscript 6 straight H subscript 5 straight C with minus on top straight H subscript 2 greater than thin space left parenthesis CH subscript 3 right parenthesis subscript 2 straight C with minus on top straight H greater than thin space left parenthesis CH subscript 3 right parenthesis subscript 3 straight C with minus on top space