MODIFIED MASTERING CHEMISTRY W/ ETEXT
8th Edition
ISBN: 9781323782507
Author: Bruice
Publisher: PEARSON
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Chapter 21.3, Problem 6P
Interpretation Introduction
Interpretation:
Reason for the carboxylic group of the amino acid is more acidic than a carboxylic acid of acetic acid has to be given.
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
The compound exists primarily in the acidic form in solutions that are more acidic than their
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Chapter 21 Solutions
MODIFIED MASTERING CHEMISTRY W/ ETEXT
Ch. 21.1 - a. Explain why, when the imidazole ring of...Ch. 21.2 - a. Which isomer(R)-alanine or (S)-alanineis...Ch. 21.2 - Prob. 4PCh. 21.3 - Prob. 5PCh. 21.3 - Prob. 6PCh. 21.3 - Draw the predominant form for glutamate in a...Ch. 21.3 - a. Why is the pKa of the glutamate side chain...Ch. 21.4 - Calculate the pI of each of the following amino...Ch. 21.4 - a. Which amino acid has the lowest pI value? b....Ch. 21.4 - Prob. 12P
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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- Ka for boric acid is 7.3 x 10¯10. What is the pKa of boric acid? A 4.86 B 9.14 C 8.66 D -4.86arrow_forwardThe dissociation of lactic acid to lactate is shown in the reaction. Lactic acid has a pKa of 3.86. A solution containing a mixture of lactic acid and lactate was found to have a pH of 5.10. Calculate the ratio of the lactic acid concentration to the lactate concentration in this solution.arrow_forwardPentapeptide has a sequence GRIND -Draw the pentapeptide in its proper ionization state at pH 7.0 -What is the pI of the pentapeptidearrow_forward
- Calculate the isoelectric point for below amino acid. asparagine: pKa (COOH) = 2.02; pKa (α-NH3+) = 8.80arrow_forwardWhy is the pK of the carboxyl group of glycine (pK = 2.3) less than that for acetic acid (pK = 4.76)?arrow_forwardCalculate the percentage of free acid for (a) phenobarbital (it is an acid with pKa = 7.40) and (b) hexobarbital (also an acid with pKa = 8.4) at the physiological condition of pH 7.4.arrow_forward
- A naturally occurring amino acid such as alanine has a group that is a carboxylic acid and a group that is a protonated amine. a. If the pKa value of a carboxylic acid such as acetic acid is about 5 (see Table 2.1), then why is the pKa value of the carboxylic acid group of alanine so much lower? b. Draw the structure of alanine in a solution at pH = 0. c. Draw the structure of alanine in a solution at physiological pH (pH 7.4). d. Draw the structure of alanine in a solution at pH = 12. e. Is there a pH at which alanine is uncharged (that is, neither group has a charge)? f. At what pH does alanine have no net charge (that is, the amount of negative charge is the same as the amount of positive charge)?arrow_forwardCalculate the isoelectric point for each amino acid.a. cysteine: pKa (COOH) = 2.05; pKa (a-NH3+) = 10.25b. methionine: pKa (COOH) = 2.28; pKa (a-NH3+) = 9.21arrow_forwardThis amino acid has a pK1 = 2.36 and pK2 = 9.68. Its pH is … a. 12.04 b. 6.02 c. 6.00 d. 7.32arrow_forward
- Consider the amino acid and its pKa values:Lysine: pKa1= 2.18 pKa2= 8.95, pKaR=10.79 a. Calculate the isoelectric point.b. What will be the net charge on lysine at the isoelectric point?c. In what direction will the lysine move when placed in an electric field at a pH value of 6.68d. Which form of the lysine is the least soluble in water?e. Draw the structure of the lysine which is the least soluble in water?arrow_forwardWhy is protonated pyrimidine (pKa = 1.0) more acidic than protonated pyridine (pKa = 5.2)?arrow_forwardIf an amino acid has pKa1 = 2.71 and pKa2 = 9.31, at what pH value in aqueous solution would the predominant form of this amino acid be a zwitterion? Please explain your answer and show your work. a) 6.01 b) 2.71 c) 5.65 d) 12.02 e) 9.31arrow_forward
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