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. HOEtgNPhenolTriethylamine Table 23.2 Acid Strengths, pK, of the Conjugate Acids of Selected AminesAmineStructurepk, of Conjugate AcldAmmoniaNH,9.26Primary AminesMethylamineCH,NH,10.64EthylamineCH,CH,NH,10.81CyclohexylamineCH,NH,10.66Secondary AminesDimethylamlne(CH),NH10.73Diethylamine(CH,CH,),NH10.98Tertiary AminesTrimethylamine(CH,),N9.81Triethylamine(CH,CH,),N10.75Aromatic AminesAniline-NH,4.634-MethylanilineCH,-NH25.084-ChloroanlineCI-NH24.154-NitroanllineO,N--NH,1.0Aromatic Heterocyclic AminesPyridine5.25Imidazole6.95

of an acid is a measure of its strength. It is given by the expression where is the dissociation…

Answered: HO EtgN Phenol Triethylamine Table…

Introduction to General, Organic and Biochemistry

11th Edition

ISBN:9781285869759

Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres

Chapter21: Lipids

Section: Chapter Questions

Problem 21.40P

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Question

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.

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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