HO EtgN Phenol Triethylamine Table 23.2 Acid Strengths, pK, of the Conjugate Acids of Selected Amines Amine Structure pk, of Conjugate Acld Ammonia NH, 9.26 Primary Amines Methylamine CH,NH, 10.64 Ethylamine CH,CH,NH, 10.81 Cyclohexylamine CH,NH, 10.66 Secondary Amines Dimethylamlne (CH),NH 10.73 Diethylamine (CH,CH,),NH 10.98 Tertiary Amines Trimethylamine (CH,),N 9.81 Triethylamine (CH,CH,),N 10.75 Aromatic Amines Aniline -NH, 4.63 4-Methylaniline CH, -NH2 5.08 4-Chloroanline CI- NH2 4.15 4-Nitroanlline O,N- -NH, 1.0 Aromatic Heterocyclic Amines Pyridine 5.25 Imidazole 6.95

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Complete the following acid-base reactions and predict the direction of equilibrium (to the right or to the left) for each. Justify your prediction by citing values of pKa for the stronger and weaker acid in each equilibrium. For values of acid ionization constants, consult Table 23.2 (Acid Strengths, pKa, of the Conjugate Acids of Selected Amines) and Appendix 2 (Acid Ionization Constants for the Major Classes of Organic Acids). Where no ionization constants are given, make the best estimate from the information given in the reference tables and sections.

HO
EtgN
Phenol
Triethylamine
Transcribed Image Text:HO EtgN Phenol Triethylamine
Table 23.2 Acid Strengths, pK, of the Conjugate Acids of Selected Amines
Amine
Structure
pk, of Conjugate Acld
Ammonia
NH,
9.26
Primary Amines
Methylamine
CH,NH,
10.64
Ethylamine
CH,CH,NH,
10.81
Cyclohexylamine
CH,NH,
10.66
Secondary Amines
Dimethylamlne
(CH),NH
10.73
Diethylamine
(CH,CH,),NH
10.98
Tertiary Amines
Trimethylamine
(CH,),N
9.81
Triethylamine
(CH,CH,),N
10.75
Aromatic Amines
Aniline
-NH,
4.63
4-Methylaniline
CH,
-NH2
5.08
4-Chloroanline
CI-
NH2
4.15
4-Nitroanlline
O,N-
-NH,
1.0
Aromatic Heterocyclic Amines
Pyridine
5.25
Imidazole
6.95
Transcribed Image Text:Table 23.2 Acid Strengths, pK, of the Conjugate Acids of Selected Amines Amine Structure pk, of Conjugate Acld Ammonia NH, 9.26 Primary Amines Methylamine CH,NH, 10.64 Ethylamine CH,CH,NH, 10.81 Cyclohexylamine CH,NH, 10.66 Secondary Amines Dimethylamlne (CH),NH 10.73 Diethylamine (CH,CH,),NH 10.98 Tertiary Amines Trimethylamine (CH,),N 9.81 Triethylamine (CH,CH,),N 10.75 Aromatic Amines Aniline -NH, 4.63 4-Methylaniline CH, -NH2 5.08 4-Chloroanline CI- NH2 4.15 4-Nitroanlline O,N- -NH, 1.0 Aromatic Heterocyclic Amines Pyridine 5.25 Imidazole 6.95
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