EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 21.3, Problem 6P
Interpretation Introduction
Interpretation:
Reason for the carboxylic group of the amino acid is more acidic than a
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
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
In 0.1M solution glycine (pKa 9.6) at pH of 9.0, what fraction of glycine has its amino group in the -NH3+ form?
The pKa of formic acid is 3.75. What is the Ka of formic acid?
4a) Canavanine is an amino acid that is produced by some legume plants. It is not used in proteins but serves as a nitrogen storage molecule in seeds, and is being investigated as a possible anti-cancer and anti-viral drug. Canavanine's amino and carboxyl groups are the same as those in any other amino acid (pKa for the amino group is 8.0 and pKa for the carboxyl group is 3.1), and its side group has a single ionizable group with a pKa of 7.0. Describe or explain what that statement (the previous sentence) tells you about the protonation state of each of the 3 ionizable groups on this amino acid if it is dissolved in pure distilled water at pH 7.0.
Chapter 21 Solutions
EBK ORGANIC CHEMISTRY
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...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 22-59 What is the effect of salt bridges on the tertiary structure of proteins?arrow_forwardProvide an explanation without using the pka values : Why is phenol stronger acid than butanoic acid?arrow_forwardNet Charge on an Amino Group.The amino acid glycine has hydrogen as its side-chain (R) group. Values of pKca= 2:36 and pKaa=9:56 have been previously reported for glycine. Superscripts c, a, and s refer to a-carboxylic acid, α-amino base, and side chain, respectively. Using these values, determine the net charge on the a-amino group of glycine at a physiologic pH of 7.2 and a pH of 3 [70].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 pKa of each acid and indicate which is the stronger acid. C6O2H8, Ka = 1.7 x 10–5 C2O4H2, Ka = 5.9 x 10–2arrow_forwardLysine and tryptophan are two amino acids that contain an additional N atom in the R group bonded to the a carbon. While lysine is classified as a basic amino acid because it contains an additional basic N atom, tryptophan is classified as a neutral amino acid. Explain why this difference in classification occurs.arrow_forward
- The pkb of methylamine, CH3NH2, is 3.36. Calculate the pka of its conjugate acid, CH3NH3*. pka =arrow_forward2. Classify the following amino acids as nonpolar, polar basic, polar acidic, or polar neutral. (a) (b) (c) (d) H₂N-CH-COH CH-OH I CH3 || H₂N-CH-C-OH I CH₂ C=O 1 OH H₂N-CH-C-OH CH₂ T CH-CH3 CH₂ H₂N-CH-C-OH ī CH₂ OH 229arrow_forwardComplete the table for the ionizable groups of the fictitious amino acid hypothetinine. pka (to TWO decimals) Average charge of group when pH=pK (to ONE decimal) Group Ka alpha-carboxyl 1.38 x 103 alpha-amino 6.02 x 10-10arrow_forward
- Consider the amino acid valine, whose pKavalues are given below. (a) Draw the major form of valine when in a solution of pH = 6.0. (b) Draw the major form of valine when in a solution of pH = 12.0arrow_forwardPentapeptide has a sequence GRIND -Draw the pentapeptide in its proper ionization state at pH 7.0 -What is the pI of the pentapeptidearrow_forwardVhuhhhharrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistry: An Atoms First ApproachChemistryISBN:9781305079243Author:Steven S. Zumdahl, Susan A. ZumdahlPublisher:Cengage Learning
- World of ChemistryChemistryISBN:9780618562763Author:Steven S. ZumdahlPublisher:Houghton Mifflin College DivChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage LearningIntroduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry: An Atoms First Approach
Chemistry
ISBN:9781305079243
Author:Steven S. Zumdahl, Susan A. Zumdahl
Publisher:Cengage Learning
World of Chemistry
Chemistry
ISBN:9780618562763
Author:Steven S. Zumdahl
Publisher:Houghton Mifflin College Div
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning