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Draw the form of l-glutamic acid that predominates at each

Chapter 25, Problem 25.47

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QUESTION:

Draw the form of l-glutamic acid that predominates at each pH: (a) 1.9 (b) 2.4 (c) 5.8 (d) 10.4

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QUESTION:

Draw the form of l-glutamic acid that predominates at each pH: (a) 1.9 (b) 2.4 (c) 5.8 (d) 10.4

ANSWER:

Step 1 of 5

The structure of L-glutamic acid is:

     

L-Glutamic acid has three sites which contain acidic / basic protons: the two carboxylic acids and one amine group. The carboxylic acid has a \(\mathrm{pK_a}\) value of 2.10, the ammonium group has a \(\mathrm{pK_a}\) value of 9.67, and the side chain (the other carboxylic acid) has a \(\mathrm{pK_a}\) value of 4.25. If the pH is below a given \(\mathrm{pK_a}\) value, the species with that \(\mathrm{pK_a}\) value will exist predominately in its protonated form.

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