Phenol (pKa = 10.0) and benzoic acid (pKa = 4.2) both have acidic protons, although benzoic acid is a stronger acid than phenol. If phenol and benzoic acid were both dissolved in dichloromethane, and you added 3 M NaHCO3, which one of the following choices correctly describes which compound(s) would participate in an acid-base reaction with 3M NaHCO3? Note that the pKa of carbonic acid (H2CO3, the conjugate acid of hydrogen carbonate) is 6.3, and the pKa of water is ~15.7. он phenol pka = 10.0 benzoic acid pKa = 4.2 3 M NaHCO3would selectively deprotonate benzoic acid but not phenol. 3 M NaHCO3would deprotonate BOTH benzoic acid and phenol. 3 M NaHCO3would selectively deprotonate phenol but not benzoic acid. O None of the above.

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Phenol (pKa = 10.0) and benzoic acid (pKa = 4.2) both have acidic protons,
although benzoic acid is a stronger acid than phenol. If phenol and benzoic acid
were both dissolved in dichloromethane, and you added 3 M NaHCO3, which one of
the following choices correctly describes which compound(s) would participate in an
acid-base reaction with 3M NaHCO3? Note that the pKa of carbonic acid (H2CO3,
the conjugate acid of hydrogen carbonate) is 6.3, and the pKa of water is ~15.7.
OH
phenol
pKa = 10.0
benzoic acid
pKa = 4.2
3 M NaHCO3would selectively deprotonate benzoic acid but not phenol.
3 M NaHCO3would deprotonate BOTH benzoic acid and phenol.
3 M NaHCO3would selectively deprotonate phenol but not benzoic acid.
O None of the above.
Transcribed Image Text:Phenol (pKa = 10.0) and benzoic acid (pKa = 4.2) both have acidic protons, although benzoic acid is a stronger acid than phenol. If phenol and benzoic acid were both dissolved in dichloromethane, and you added 3 M NaHCO3, which one of the following choices correctly describes which compound(s) would participate in an acid-base reaction with 3M NaHCO3? Note that the pKa of carbonic acid (H2CO3, the conjugate acid of hydrogen carbonate) is 6.3, and the pKa of water is ~15.7. OH phenol pKa = 10.0 benzoic acid pKa = 4.2 3 M NaHCO3would selectively deprotonate benzoic acid but not phenol. 3 M NaHCO3would deprotonate BOTH benzoic acid and phenol. 3 M NaHCO3would selectively deprotonate phenol but not benzoic acid. O None of the above.
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