Skip to main content
deleted 19 characters in body
Source Link
M.A.R.
  • 10.8k
  • 19
  • 72
  • 95

enter image description here


Above are the resonance forms of m-cresol after deprotonation. As you can see, the negative charge resonates around the aryl ring, but never resides on the carbon directly bonded to the methyl group at the meta position. 

Thus, the hyperconjugative effect from the meta methyl group does not affect the acidity of cresol in this isomer. Notice, how the destabilising hyperconjugation effect would destabilise the resonating negative charge, if the methyl group was at the orthoortho- or parapara- position.

enter image description here


Above are the resonance forms of m-cresol after deprotonation. As you can see, the negative charge resonates around the aryl ring, but never resides on the carbon directly bonded to the methyl group at the meta position. Thus, the hyperconjugative effect from the meta methyl group does not affect the acidity of cresol in this isomer. Notice, how the destabilising hyperconjugation effect would destabilise the resonating negative charge, if the methyl group was at the ortho or para position.


Above are the resonance forms of m-cresol after deprotonation. As you can see, the negative charge resonates around the aryl ring, but never resides on the carbon directly bonded to the methyl group at the meta position. 

Thus, the hyperconjugative effect from the meta methyl group does not affect the acidity of cresol in this isomer. Notice how the destabilising hyperconjugation effect would destabilise the resonating negative charge, if the methyl group was at the ortho- or para- position.

Source Link
Ava
  • 141
  • 4

enter image description here


Above are the resonance forms of m-cresol after deprotonation. As you can see, the negative charge resonates around the aryl ring, but never resides on the carbon directly bonded to the methyl group at the meta position. Thus, the hyperconjugative effect from the meta methyl group does not affect the acidity of cresol in this isomer. Notice, how the destabilising hyperconjugation effect would destabilise the resonating negative charge, if the methyl group was at the ortho or para position.