a) Para, ortho and meta nitrophenol are constitutional isomers of one another that all vary in the position of the nitro group around the ring relative to the hydroxy group. Whereas the pKa of both para and ortho-nitrophenol is virtually identical at 7.1 and 7.2 respectively, the pka of meta-nitrophenol is very different at pka = 9.3. ОН OH ОН NO2 'NO2 NO2 Ortho-nitrophenol meta-nitrophenol para-nitrophenol 1) State whether meta-nitrophenol is more or less acidic compared to ortho- or para- nitrophenol.

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2. Resonance
a) Para, ortho and meta nitrophenol are constitutional isomers of one another that all vary in
the position of the nitro group around the ring relative to the hydroxy group.
Whereas the pKa of both para and ortho-nitrophenol is virtually identical at 7.1 and 7.2
respectively, the pka of meta-nitrophenol is very different at pKa = 9.3.
ОН
OH
ОН
NO2
NO2
NO2
meta-nitrophenol
para-nitrophenol
Ortho-nitrophenol
1) State whether meta-nitrophenol is more or less acidic compared to ortho- or para-
nitrophenol.
2) Using your knowledge of resonance, structure and electronegativity explain the difference
in pka of the three different constitutional isomers.
Transcribed Image Text:2. Resonance a) Para, ortho and meta nitrophenol are constitutional isomers of one another that all vary in the position of the nitro group around the ring relative to the hydroxy group. Whereas the pKa of both para and ortho-nitrophenol is virtually identical at 7.1 and 7.2 respectively, the pka of meta-nitrophenol is very different at pKa = 9.3. ОН OH ОН NO2 NO2 NO2 meta-nitrophenol para-nitrophenol Ortho-nitrophenol 1) State whether meta-nitrophenol is more or less acidic compared to ortho- or para- nitrophenol. 2) Using your knowledge of resonance, structure and electronegativity explain the difference in pka of the three different constitutional isomers.
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