Rank the bold-faced hydrogens for the following compounds from most acidic to least acidic. The table below can be useful to answer this problem. H I Short pKa table Functional group Hydrochloric acid Carboxylic acids Protonated amines Water Alkyne Amine Alkane II co₂H Example HCI: H3C OH ee NH4CI: HO-H H₂C-CEC-H : NH3 CH4 III Stronger acid pka H Weaker acid -8 5 10 14 25 -35 -50 IV CO₂H conj. base :CI: .. H₂C : NH3 : OH R-CEC: : NH₂ CH3 Weaker base Stronger base

Fundamentals Of Analytical Chemistry
9th Edition
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Author:Skoog
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Chapter9: Aqueous Solutions And Chemical Equilibria
Section: Chapter Questions
Problem 9.20QAP
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Rank the bold-faced hydrogens for the following compounds from most acidic to least acidic. The table below can be
useful to answer this problem.
I
Short pka table
Functional group
Hydrochloric
acid
Carboxylic
acids
Protonated
amines
Water
Alkyne
Amine
Alkane
OII>IV> V> ||| > |
OIV>II>I>V > III
OV> III > IV> II > I
II
CI
co₂H
Stronger
Example acid pka
HCI:
H3C
NHÀ :C
HO-H
H3C-CEC-H
: NH3
III
CH4
Weaker
acid
-8
5
10
14
25
-35
~50
IV
CO₂H
conj. base
:CI:
H₂C
: NH3
e..
: OH
R-CEC:
: NH₂
CH3
V
Weaker
base
Stronger
base
H
Transcribed Image Text:Rank the bold-faced hydrogens for the following compounds from most acidic to least acidic. The table below can be useful to answer this problem. I Short pka table Functional group Hydrochloric acid Carboxylic acids Protonated amines Water Alkyne Amine Alkane OII>IV> V> ||| > | OIV>II>I>V > III OV> III > IV> II > I II CI co₂H Stronger Example acid pka HCI: H3C NHÀ :C HO-H H3C-CEC-H : NH3 III CH4 Weaker acid -8 5 10 14 25 -35 ~50 IV CO₂H conj. base :CI: H₂C : NH3 e.. : OH R-CEC: : NH₂ CH3 V Weaker base Stronger base H
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