
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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I don't get it at all. I struggled with my homework. Can you help me about the Henderson-Hasselbalch relation, summarized in the table below, it is possible to predict the predominant form of these groups at a particular pH? Draw the line bond structure for the general form of an amino acid using "R" to represent the side chain. Draw the N- and C-terminus groups using the forms that are predominant at physiological pH (pH = 7.4. Include lone pairs in your drawing.

Transcribed Image Text:13.2) Draw the line bond structure for the general form of an amino acid using “R” to represent the side chain. Draw the N- and C-
terminus groups using the forms that are predominant at physiological pH (pH = 7.4). Include lone pairs in your drawing.
quaternary ammonium group
Quaternary ammonium groups that are
attached to the a-carbons of amino
acids have pK₂ values of about 9.5,
therefore, at pH = 7.4, the acid form
(quaternary ammonium group) is
predominant.
ANSWER:
H :0:
||
H-N—C—C—0:
H
H
R
carboxylate group
The pKa values of amino acid
carboxyl groups are between 2 and 5
(depending on which amino acid),
therefore, at pH = 7.4, the base form
(carboxylate ion) is predominant.
R-group
(called "side-chain")
![Draw the line bond structure for the general form of an amino acid using "R" to represent the side chain. Draw the N- and C-
terminus groups using the forms that are predominant at physiological pH (pH = 7.4). Include lone pairs in your drawing.
HINT:
The structure of the predominant form of an amino acid will depend on the pH because amino acids
involve the carboxyl group/carboxylate group conjugate pair and the quaternary ammonium
group/amine group conjugate pair. Using the implications of the the Henderson-Hasselbalch
relation, summarized in the table below, it is possible to predict the predominant form of these
groups at a particular pH.
Solution
Condition
pH <pka
pH > pKa
pH = pka
Relative Amounts of
Acid and Base Forms
[HA] > [A-]
[A-] > [HA]
[HA] = [A-]
The pK₂ values of amino acid carboxyl groups are between 2 and 5 (depending on which amino
acid), therefore, at pH = 7.4, the base form (carboxylate ion) is predominant.
Quaternary ammonium groups that are attached to the a-carbons of amino acids have pk₁ values of
about 9.5, therefore, at pH = 7.4, the acid form (quaternary ammonium group) is predominant.](https://content.bartleby.com/qna-images/question/3442c249-7c73-43ca-b651-caace2a5bb24/7b70351f-1657-451c-9025-3cfa72cb8d1e/pmikoqg_thumbnail.png)
Transcribed Image Text:Draw the line bond structure for the general form of an amino acid using "R" to represent the side chain. Draw the N- and C-
terminus groups using the forms that are predominant at physiological pH (pH = 7.4). Include lone pairs in your drawing.
HINT:
The structure of the predominant form of an amino acid will depend on the pH because amino acids
involve the carboxyl group/carboxylate group conjugate pair and the quaternary ammonium
group/amine group conjugate pair. Using the implications of the the Henderson-Hasselbalch
relation, summarized in the table below, it is possible to predict the predominant form of these
groups at a particular pH.
Solution
Condition
pH <pka
pH > pKa
pH = pka
Relative Amounts of
Acid and Base Forms
[HA] > [A-]
[A-] > [HA]
[HA] = [A-]
The pK₂ values of amino acid carboxyl groups are between 2 and 5 (depending on which amino
acid), therefore, at pH = 7.4, the base form (carboxylate ion) is predominant.
Quaternary ammonium groups that are attached to the a-carbons of amino acids have pk₁ values of
about 9.5, therefore, at pH = 7.4, the acid form (quaternary ammonium group) is predominant.
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