The pk, of phenol (C,H5OH) is 10.0. When a methyl (CH3) group is attached to the ring, the pK, increases, as shown here for the ortho, meta, and para isomers. OH ОН ОН ОН CH3 (a) Explain why the pk, values of all three isomers are higher than the pk, of phenol itself. (b) Explain why the meta isomer has the lowest pk, of CH3 Phenol CH3 the three isomers. pKa = 10.0 10.3 10.1 10.2

Organic Chemistry
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ISBN:9781305080485
Author:John E. McMurry
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Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
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Problem 25VC: The following molecular model of a dimethyl-substituted biphenyl represents the lowest-energy...
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The pk, of phenol (C,H5OH) is 10.0. When a methyl (CH3)
group is attached to the ring, the pK, increases, as shown
here for the ortho, meta, and para isomers.
OH
ОН
ОН
ОН
CH3
(a) Explain why the pk, values of all three isomers are
higher than the pk, of phenol itself.
(b) Explain why the meta isomer has the lowest pk, of
CH3
Phenol
CH3
the three isomers.
pKa
= 10.0
10.3
10.1
10.2
Transcribed Image Text:The pk, of phenol (C,H5OH) is 10.0. When a methyl (CH3) group is attached to the ring, the pK, increases, as shown here for the ortho, meta, and para isomers. OH ОН ОН ОН CH3 (a) Explain why the pk, values of all three isomers are higher than the pk, of phenol itself. (b) Explain why the meta isomer has the lowest pk, of CH3 Phenol CH3 the three isomers. pKa = 10.0 10.3 10.1 10.2
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