Essential Organic Chemistry (3rd Edition)
Essential Organic Chemistry (3rd Edition)
3rd Edition
ISBN: 9780321937711
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 17.3, Problem 6P

(a)

Interpretation Introduction

Interpretation:

The predominant form of glutamate at pH (0) should be drawn.

Concept Introduction:

Acid-base properties of Amino acids:

 Every amino acid has a carbonyl group and an amino group, and each group can exist in an acidic form or a basic form, depending on pH of the solution in which the amino acid is dissolved.

The compound exists primarily in the acidic form in solutions that are more acidic than their pKa values, and primarily in the basic form (without their protons) in solutions that are more basic than their pKa values.

At pH=7, pH of the solution is greater than the pKa of the carboxyl group then carboxyl group is in the basic form, but less than the pKa of the protonated amino group then amino acid is in the acidic form.

(b)

Interpretation Introduction

Interpretation:

The predominant form of glutamate at pH (3) should be drawn.

Concept Introduction:

Acid-base properties of Amino acids:

Every amino acid has a carbonyl group and an amino group, and each group can exist in an acidic form or a basic form, depending on pH of the solution in which the amino acid is dissolved.

The compound exists primarily in the acidic form in solutions that are more acidic than their pKa values, and primarily in the basic form (without their protons) in solutions that are more basic than their pKa values.

At pH=7, pH of the solution is greater than the pKa of the carboxyl group then carboxyl group is in the basic form, but less than the pKa of the protonated amino group then amino acid is in the acidic form.

(c)

Interpretation Introduction

Interpretation:

The predominant form of glutamate at pH (6) should be drawn.

Concept Introduction:

Acid-base properties of Amino acids:

 Every amino acid has a carbonyl group and an amino group, and each group can exist in an acidic form or a basic form, depending on pH of the solution in which the amino acid is dissolved.

The compound exists primarily in the acidic form in solutions that are more acidic than their pKa values, and primarily in the basic form (without their protons) in solutions that are more basic than their pKa values.

At pH=7, pH of the solution is greater than the pKa of the carboxyl group then carboxyl group is in the basic form, but less than the pKa of the protonated amino group then amino acid is in the acidic form.

(d)

Interpretation Introduction

Interpretation:

The predominant form of glutamate at pH (11) should be drawn.

Concept Introduction:

Acid-base properties of Amino acids:

 Every amino acid has a carbonyl group and an amino group, and each group can exist in an acidic form or a basic form, depending on pH of the solution in which the amino acid is dissolved.

The compound exists primarily in the acidic form in solutions that are more acidic than their pKa values, and primarily in the basic form (without their protons) in solutions that are more basic than their pKa values.

At pH=7, pH of the solution is greater than the pKa of the carboxyl group then carboxyl group is in the basic form, but less than the pKa of the protonated amino group then amino acid is in the acidic form.

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Students have asked these similar questions
Draw the predominant form for glutamate in a solution with the following pH: a. 0 b. 3 c. 6 d. 11
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Chapter 17 Solutions

Essential Organic Chemistry (3rd Edition)

Ch. 17.5 - Prob. 12PCh. 17.6 - Prob. 13PCh. 17.6 - What amino acid would be formed using the...Ch. 17.6 - What amino acid would be formed when the aldehyde...Ch. 17.7 - Pig liver esterase is an enzyme that catalyzes the...Ch. 17.8 - Prob. 17PCh. 17.8 - Prob. 18PCh. 17.8 - Prob. 19PCh. 17.8 - Prob. 20PCh. 17.10 - Prob. 21PCh. 17.10 - Prob. 22PCh. 17.10 - Why does cyanogen bromide not cleave on the C-side...Ch. 17.10 - Prob. 24PCh. 17.10 - Prob. 26PCh. 17.12 - Prob. 27PCh. 17.13 - a. Which would have the greatest percentage of...Ch. 17 - Draw the predominant form of the following amino...Ch. 17 - What is the pI of serine?Ch. 17 - Prob. 31PCh. 17 - Prob. 32PCh. 17 - Which would have a higher percentage of negative...Ch. 17 - Draw the form of aspartate that predominates at...Ch. 17 - Prob. 35PCh. 17 - A professor was preparing a manuscript for...Ch. 17 - a. Why is the pKa of the glutamate side chain...Ch. 17 - Prob. 38PCh. 17 - Determine the amino acid sequence of a polypeptide...Ch. 17 - Prob. 40PCh. 17 - Prob. 41PCh. 17 - Three peptides were obtained from a trypsin...Ch. 17 - Prob. 43PCh. 17 - After the polypeptide shown here was treated with...Ch. 17 - The disulfide bridges of a polypeptide were...Ch. 17 - -Amino acids can be prepared by treating an...Ch. 17 - Reaction of a polypeptide with carboxypeptidase A...Ch. 17 - Prob. 48PCh. 17 - Prob. 49PCh. 17 - Show how valine can be prepared by a. a Strecker...Ch. 17 - Prob. 51PCh. 17 - Why is proline never found in an -helix?Ch. 17 - Determine the amino acid sequence of a polypeptide...Ch. 17 - Prob. 55PCh. 17 - A chemist wanted to test his hypothesis that the...Ch. 17 - A normal polypeptide and a mutant of the...
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