Explain why the pKa of p-nitrophenol is 7.14, whereas the pKa of m-nitrophenol is 8.39. Explain why the of p-nitrophenol is 7.14, whereas the of m-nitrophenol is 8.39. When para-nitrophenol loses a proton, the negative charge in the conjugate base can be delocalized onto the nitro substituent. When meta-nitrophenol loses a proton, the negative charge cannot be delocalized onto the nitro substituent. When para-nitrophenol loses a proton, the negative charge on the oxygen atom of the nitro group can be delocalized onto the benzene ring. When meta-nitrophenol loses a proton, the negative charge on the oxygen atom of the nitro group cannot be delocalized onto the benzene ring. When para-nitrophenol loses a proton, the negative charge in the conjugate base cannot be delocalized onto the nitro substituent. When meta-nitrophenol loses a proton, the negative charge can be delocalized onto the nitro substituent. When para-nitrophenol loses a proton, the negative charge on the oxygen atom of the nitro group cannot be delocalized onto the benzene ring. When meta-nitrophenol loses a proton, the negative charge on the oxygen atom of the nitro group can be delocalized onto the benzene ring.