Question

Расположите в ряд по уменьшению кислотности следующие соединения: а) этанол, этантиол, этиламин; б) фенол, п-нитрофенол, п-аминофенол; в) этанол, пропанол-2, метанол, 2-метилпропанол-2. Обоснуйте решение, исходя из стабильности анионов

Answer 1

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Answer 2

Ordering Compounds by Decreasing Acidity

To determine the order of compounds based on decreasing acidity, we need to consider the stability of the corresponding anions. The more stable the anion, the stronger the acid. Let's analyze each set of compounds separately:

a) Ethanol, Ethanethiol, Ethylamine: - Ethanol (CH3CH2OH) is a weak acid because it can donate a proton (H+) to form the ethoxide ion (CH3CH2O-). - Ethanethiol (CH3CH2SH) is a stronger acid than ethanol because it can donate a proton to form the ethanethiolate ion (CH3CH2S-). - Ethylamine (CH3CH2NH2) is the strongest acid among the three because it can donate a proton to form the ethylammonium ion (CH3CH2NH3+). Therefore, the compounds can be ordered from least acidic to most acidic as follows: ethanol < ethanethiol < ethylamine.

b) Phenol, p-Nitrophenol, p-Aminophenol: - Phenol (C6H5OH) is a weak acid because it can donate a proton to form the phenoxide ion (C6H5O-). - p-Nitrophenol (C6H4NO3OH) is a stronger acid than phenol because it can donate a proton to form the p-nitrophenoxide ion (C6H4NO3O-). - p-Aminophenol (C6H4NH2OH) is the strongest acid among the three because it can donate a proton to form the p-aminophenoxide ion (C6H4NH2O+). Therefore, the compounds can be ordered from least acidic to most acidic as follows: phenol < p-nitrophenol < p-aminophenol.

c) Ethanol, 2-Propanol, Methanol, 2-Methylpropan-2-ol: - Ethanol (CH3CH2OH) is a weak acid because it can donate a proton to form the ethoxide ion (CH3CH2O-). - 2-Propanol (CH3CH(OH)CH3) is a weaker acid than ethanol because it can donate a proton to form the 2-propanoxide ion (CH3CH(O-)CH3). - Methanol (CH3OH) is a stronger acid than 2-propanol because it can donate a proton to form the methoxide ion (CH3O-). - 2-Methylpropan-2-ol (CH3C(CH3)2OH) is the strongest acid among the four because it can donate a proton to form the 2-methylpropan-2-oxide ion (CH3C(CH3)2O-). Therefore, the compounds can be ordered from least acidic to most acidic as follows: ethanol < 2-propanol < methanol < 2-methylpropan-2-ol.

In summary, the compounds can be ordered by decreasing acidity as follows: a) Ethanol < Ethanethiol < Ethylamine b) Phenol < p-Nitrophenol < p-Aminophenol c) Ethanol < 2-Propanol < Methanol < 2-Methylpropan-2-ol.

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