Organic Chemistry, Books a la Carte Edition (8th Edition)
Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Chapter 21, Problem 49P

Glycine has pK2 values of 2.34 and 9.60. At what pH does glycine exist in the forms shown?

Chapter 21, Problem 49P, Glycine has pK2 values of 2.34 and 9.60. At what pH does glycine exist in the forms shown?

(a)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The pH at which glycine exists at the given form has to be calculated.

Concept introduction:

The isoelectric point (pI) is the pH at which the amount of positive charge and negative charge on an amino acid becomes balanced.

The value of pI is depends upon the pKa value of protonated amino group and pKa value of carboxyl group of an amino acid.

Protons are released when the pH becomes pKa of species.

Answer to Problem 49P

The pH of the glycine for the given form is 9.60.

Explanation of Solution

In the given form of glycine,

Organic Chemistry, Books a la Carte Edition (8th Edition), Chapter 21, Problem 49P , additional homework tip  1

The 50% of amino group of the glycine are released their protons, so the pH of the system becomes pKa.

The pKa of the amino group of glycine is 9.60.

Therefore,

The pH of the glycine for the given form is 9.60.

(b)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The pH at which glycine exists at the given form has to be calculated.

Concept introduction:

The isoelectric point (pI) is the pH at which the amount of positive charge and negative charge on an amino acid becomes balanced.

The value of pI is depends upon the pKa value of protonated amino group and pKa value of carboxyl group of an amino acid.

Protons are released when the pH becomes pKa of species.

Explanation of Solution

In the given form of glycine,

Organic Chemistry, Books a la Carte Edition (8th Edition), Chapter 21, Problem 49P , additional homework tip  2

The amount of positive charge and negative charge are equal or balanced for 100% system.

The isoelectric point (pI) is the pH at which the amount of positive charge and negative charge on an amino acid becomes balanced.

Therefore,

The pH of the glycine for the given form is 6.02.

(c)

Expert Solution
Check Mark
Interpretation Introduction

Interpretation:

The pH at which glycine exists at the given form has to be calculated.

Concept introduction:

The isoelectric point (pI) is the pH at which the amount of positive charge and negative charge on an amino acid becomes balanced.

The value of pI is depends upon the pKa value of protonated amino group and pKa value of carboxyl group of an amino acid.

Protons are released when the pH becomes pKa of species.

Answer to Problem 49P

The pH of the glycine for the given form is 2.34.

Explanation of Solution

In the glycine form of glycine,

Organic Chemistry, Books a la Carte Edition (8th Edition), Chapter 21, Problem 49P , additional homework tip  3

The 50% of –OH group of the glycine are released their protons, so the pH of the system becomes pKa of the –OH of glycine.

The pKa of the –OH group of glycine is 2.34.

Therefore,

The pH of the glycine for the given form is 2.34.

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Chapter 21 Solutions

Organic Chemistry, Books a la Carte Edition (8th Edition)

Ch. 21.4 - Prob. 13PCh. 21.4 - Explain why the pI of lysine is the average of the...Ch. 21.5 - What aldehyde is formed when valine is treated...Ch. 21.5 - Prob. 16PCh. 21.5 - Prob. 17PCh. 21.5 - Prob. 18PCh. 21.5 - Prob. 19PCh. 21.6 - Why is excess ammonia used in the preceding...Ch. 21.6 - Prob. 21PCh. 21.6 - What amino acid is formed using the...Ch. 21.6 - Prob. 23PCh. 21.6 - What amino acid is formed when the aldehyde used...Ch. 21.7 - Esterase is an enzyme that catalyzes the...Ch. 21.8 - Draw the tetrapeptide Ala-Thr-Asp-Asn and indicate...Ch. 21.8 - Draw the resonance contributors of the peptide...Ch. 21.8 - Which bonds in the backbone of a peptide can...Ch. 21.9 - An opioid pentapeptide has the following...Ch. 21.9 - What is the configuration about each of the...Ch. 21.9 - Glutathione is a tripeptide whose function is to...Ch. 21.10 - What dipeptides would be formed by heating a...Ch. 21.10 - Suppose you are trying to synthesize the dipeptide...Ch. 21.10 - Show the steps in the synthesis of the...Ch. 21.10 - a. Calculate the overall yield of bradykinin when...Ch. 21.11 - Show the steps in the synthesis of the...Ch. 21.13 - Prob. 37PCh. 21.13 - In determining the primary structure of insulin,...Ch. 21.13 - A decapeptide undergoes partial hydrolysis to give...Ch. 21.13 - Explain why cyanogen bromide does not cleave on...Ch. 21.13 - Indicate the peptides produced from cleavage by...Ch. 21.14 - Prob. 43PCh. 21.14 - Three peptides were obtained from a trypsin...Ch. 21.14 - Prob. 45PCh. 21.15 - How would a protein that resides in the nonpolar...Ch. 21.16 - a. Which would have the greatest percentage of...Ch. 21.17 - When apples that have been cut are exposed to...Ch. 21 - Glycine has pK2 values of 2.34 and 9.60. At what...Ch. 21 - Prob. 50PCh. 21 - A titration curve is a plot of the pH of a...Ch. 21 - Prob. 52PCh. 21 - Aspartame (its structure is on page 1007) has a pl...Ch. 21 - Draw the form of aspartate that predominates at...Ch. 21 - Show how phenylalanine can be prepared by...Ch. 21 - A professor was preparing a manuscript for...Ch. 21 - What aldehydes are formed when the following amino...Ch. 21 - Prob. 58PCh. 21 - Determine the amino acid sequence of a polypeptide...Ch. 21 - Prob. 60PCh. 21 - Prob. 61PCh. 21 - Which is the more effective buffer at...Ch. 21 - Identify the location and type of charge on the...Ch. 21 - Draw the product obtained when a lysine side chain...Ch. 21 - After the polypeptide shown below was treated with...Ch. 21 - Treatment of a polypeptide with 2-mercaptoethanol...Ch. 21 - Show how aspartame can be synthesized using DCCD.Ch. 21 - -Amino acids can be prepared by treating an...Ch. 21 - Reaction of a polypeptide with carboxypeptidase A...Ch. 21 - a. How many different octapeptides can be made...Ch. 21 - Glycine has pKa values of 2.3 and 9.6. Do you...Ch. 21 - A mixture of 15 amino acids gave the fingerprint...Ch. 21 - Write the mechanism for the reaction of an amino...Ch. 21 - Prob. 74PCh. 21 - Show how valine can be prepared by a. a...Ch. 21 - The primary structure of -endorphin, a peptide...Ch. 21 - A chemist wanted to test his hypothesis that the...Ch. 21 - Propose a mechanism for the rearrangement of the...Ch. 21 - A normal polypeptide and a mutant of the...Ch. 21 - Determine the amino acid sequence of a polypeptide...
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