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Answer: A typical amino acid with one amino group and one

Chapter , Problem 100IE

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QUESTION:

A typical amino acid with one amino group and one carboxylic acid group, such as serine, can exist in water in several ionic forms. (a) Suggest the forms of the amino acid at low pH and at high pH. (b) Amino acids generally have two \(\mathrm{p} K_{a}\) values, one in the range of 2 to 3 and the other in the range of 9 to 10. Serine, for example, has \(\mathrm{p} K_{a}\) values of 2.19 and 9.21. Using species such as acetic acid and ammonia as models, suggest the origin of the two \(\mathrm{p} K_{a}\) values. (c) Glutamic acid is an amino acid that has three \(\mathrm{p} K_{a}\)’s: 2.10, 4.07, and 9.47. Draw the structure of glutamic acid, and assign each \(\mathrm{p} K_{a}\) to the appropriate part of the molecule. (d) An unknown amino acid is titrated with strong base, producing the following titration curve. Which amino acids are likely candidates for the unknown?

Equation Transcription:

Text Transcription:

pK_a

pK_a

pK_a

pK_a

pK_a

Questions & Answers

QUESTION:

A typical amino acid with one amino group and one carboxylic acid group, such as serine, can exist in water in several ionic forms. (a) Suggest the forms of the amino acid at low pH and at high pH. (b) Amino acids generally have two \(\mathrm{p} K_{a}\) values, one in the range of 2 to 3 and the other in the range of 9 to 10. Serine, for example, has \(\mathrm{p} K_{a}\) values of 2.19 and 9.21. Using species such as acetic acid and ammonia as models, suggest the origin of the two \(\mathrm{p} K_{a}\) values. (c) Glutamic acid is an amino acid that has three \(\mathrm{p} K_{a}\)’s: 2.10, 4.07, and 9.47. Draw the structure of glutamic acid, and assign each \(\mathrm{p} K_{a}\) to the appropriate part of the molecule. (d) An unknown amino acid is titrated with strong base, producing the following titration curve. Which amino acids are likely candidates for the unknown?

Equation Transcription:

Text Transcription:

pK_a

pK_a

pK_a

pK_a

pK_a

ANSWER:

Step 1 of 5

In acidic conditions, the carboxylate ion takes up proton and becomes carboxylic acid, whereas the amine group becomes . At a higher pH, the amine group loses its proton and becomes , while the carboxylic group remains as a carboxylate ion.

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