Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

29. Amino Acids

Acid-Base Properties of Amino Acids

Organic Chemistry

29. Amino Acids

Acid-Base Properties of Amino Acids

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Problem 8a

Textbook Question

Draw the predominant form for glutamate in a solution with the following pH:
a. 0

Verified step by step guidance

Identify the functional groups in glutamate: Glutamate is an amino acid with an amine group (-NH₂), a carboxylic acid group (-COOH), and a side chain containing another carboxylic acid group (-COOH).

Understand the pKa values of the functional groups: The pKa values for glutamate are approximately 2.1 for the α-carboxylic acid group, 4.1 for the side chain carboxylic acid group, and 9.7 for the α-amino group.

Compare the pH of the solution (pH = 0) to the pKa values: At pH = 0, the solution is highly acidic, meaning the environment will protonate all ionizable groups in glutamate.

Determine the protonation state of each group: At pH = 0, both carboxylic acid groups (-COOH) will remain in their protonated form, and the amine group (-NH₂) will be protonated to form -NH₃⁺.

Draw the structure of glutamate in its fully protonated form: The α-carboxylic acid group and the side chain carboxylic acid group will both be -COOH, and the α-amino group will be -NH₃⁺. Ensure the correct connectivity of the molecule is shown.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Amino Acids and Their Ionization

Amino acids, like glutamate, can exist in different ionic forms depending on the pH of the solution. At low pH, amino acids tend to be protonated, meaning they carry a positive charge. Understanding the ionization of amino acids is crucial for predicting their behavior in various pH environments.

Glutamate Structure

Glutamate is an amino acid with a carboxylic acid group, an amine group, and a side chain that also contains a carboxylic acid. This structure allows glutamate to participate in acid-base reactions, influencing its charge and predominant form in solution. Recognizing its functional groups is essential for determining its ionization state.

pH and Its Effect on Charge

pH is a measure of the hydrogen ion concentration in a solution, affecting the protonation state of molecules. At a pH of 0, the environment is highly acidic, leading to an abundance of protons. This high proton concentration will influence the ionization of glutamate, resulting in a predominantly positively charged form.

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Identify the location and type of charge on the hexapeptide Lys-Ser-Asp-Cys-His-Tyr at each of the following pH values:

c. pH=7

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Draw the form of aspartate that predominates at the following pH values:

d. pH=11.0

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Draw the form of aspartate that predominates at the following pH values: c. pH=6.0

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Draw the predominant form for glutamate in a solution with the following

pH: b. 3

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c. Which amino acid has the greatest amount of negative charge at pH = 6.20?

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Draw the pH–activity profile for an enzyme that has one catalytic group at the active site:

a. the catalytic group is a general-acid catalyst with a pK_a = 5.6.

Textbook Question

Draw the pH–activity profile for an enzyme that has one catalytic group at the active site:

b. the catalytic group is a general-base catalyst with a pKa = 7.2.

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The pH–activity profile for glucose-6-phosphate isomerase indicates the participation of a group with a pK_a = 6.7 as a basic catalyst and a group with a pK_a = 9.3 as an acid catalyst. Draw the pH–activity profile and identify the amino acids that participate in the catalysis.

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Draw the predominant form for glutamate in a solution with the following pH: a. 0

Key Concepts

Amino Acids and Their Ionization

Glutamate Structure

pH and Its Effect on Charge

Watch next

Draw the predominant form for glutamate in a solution with the following pH:
a. 0