Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 26.SE, Problem 51AP
Interpretation Introduction
Interpretation:
How the protonated guanidino group in arginine is stabilized is to be explained using resonance structures.
Concept introduction:
Resonance always stabilizes a molecule. A compound with more resonance forms is more stable.
The resonance forms differ only in the position of the π bonds or the unshared pair of electrons on atoms. The position of atoms remains the same in different forms. The total number of valence electrons in all the resonance structures remains the same. Octet rule is not violated and the transfer of electrons between the bonds is indicated by curved arrows.
To explain:
Using resonance structures how the protonated guanidino group in arginine is stabilized.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
the pKa values for phenylalanine are 1.83 (carboxyl group) and 9.13 (amino group). Use the Henderson-hasselbach equation to determine the ratio of the acidic and basic forms of each of the ionizing groups of phenylalanine at neutral pH. Based on this, draw the predominant structure of phenylalanine at neutral pH.
Draw the structure of alanine in a solution at pH = 0
The pKaa of the conjugate acid of guanidine is 13.6, making it one of the strongest neutral organic bases. Offer an explanation.
Chapter 26 Solutions
Organic Chemistry
Ch. 26.1 - How many of the -amino acids shown in Table 26-1...Ch. 26.1 - Prob. 2PCh. 26.1 - Prob. 3PCh. 26.2 - Hemoglobin has pI=6.8. Does hemoglobin have a net...Ch. 26.3 - Show how you could prepare the following -amino...Ch. 26.3 - What alkyl halides would you use to prepare the...Ch. 26.3 - Prob. 7PCh. 26.4 - There are six isomeric tripeptides that contain...Ch. 26.4 - Draw the structure of M-P-V-G, and indicate its...Ch. 26.5 - Prob. 10P
Ch. 26.5 - Prob. 11PCh. 26.6 - The octapeptide angiotensin II has the sequence...Ch. 26.6 - Prob. 13PCh. 26.6 - Prob. 14PCh. 26.6 - Give the amino acid sequence of hexapeptides that...Ch. 26.7 - Prob. 16PCh. 26.7 - Write all five steps required for the synthesis of...Ch. 26.10 - Prob. 18PCh. 26.SE - Identify the following amino acids:Ch. 26.SE - Prob. 20VCCh. 26.SE - Isoleucine and threonine are the only two amino...Ch. 26.SE - Prob. 22VCCh. 26.SE - Give the sequence of the following tetrapeptide:Ch. 26.SE - Prob. 24MPCh. 26.SE - The chloromethylated polystyrene resin used for...Ch. 26.SE - Prob. 26MPCh. 26.SE - Prob. 27MPCh. 26.SE - Prob. 28MPCh. 26.SE - Except for cysteine, only S amino acids occur in...Ch. 26.SE - Prob. 30APCh. 26.SE - Prob. 31APCh. 26.SE - Show the structures of the following amino acids...Ch. 26.SE - Prob. 33APCh. 26.SE - Using both three- and one-letter codes for amino...Ch. 26.SE - Prob. 35APCh. 26.SE - Show how you could use the acetamidomalonate...Ch. 26.SE - Prob. 37APCh. 26.SE - Show how you could prepare the following amino...Ch. 26.SE - Prob. 39APCh. 26.SE - Predict the product of the reaction of valine with...Ch. 26.SE - Prob. 41APCh. 26.SE - Prob. 42APCh. 26.SE - Propose two structures for a tripeptide that gives...Ch. 26.SE - Show the steps involved in a synthesis of...Ch. 26.SE - Prob. 45APCh. 26.SE - Prob. 46APCh. 26.SE - Prob. 47APCh. 26.SE - Which of the following amino acids are more likely...Ch. 26.SE - Leuprolide is a synthetic nonapeptide used to...Ch. 26.SE - The -helical parts of myoglobin and other proteins...Ch. 26.SE - Prob. 51APCh. 26.SE - Cytochrome c is an enzyme found in the cells of...Ch. 26.SE - Prob. 53APCh. 26.SE - Prob. 54APCh. 26.SE - Prob. 55APCh. 26.SE - What is the structure of a nonapeptide that gives...Ch. 26.SE - Oxytocin, a nonapeptide hormone secreted by the...Ch. 26.SE - Aspartame, a nonnutritive sweetener marketed under...Ch. 26.SE - Prob. 59APCh. 26.SE - Prob. 60APCh. 26.SE - Prob. 61APCh. 26.SE - Prob. 62AP
Knowledge Booster
Similar questions
- What special role does the amino acid cysteine have in the peptides vasopressin and oxytocin?arrow_forward22-91 Which amino acid does not rotate the plane of polarized light?arrow_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
- Explain why the pI of lysine is the average of the pKa values of its two protonated amino groups.arrow_forwardDraw a structural formula for the form of amino acid most prevalent at pH 1.0. (a) Methioninearrow_forwardA given glycine solution was titrated against NaOH and pH of the final solution was 4.8. Given that pKa1 and pKa2 of glycine are 2.34 and 9.60, respectively. Calculate the concentration of the dissociated amino acid in terms of the undissociated amino acid, if [x] and [y] are the concentrations of dissociated and undissociated amino acid, respectively.arrow_forward
- Lysine 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_forwardPlease explain in detail how you get the net charge of the amino acid chain and everything please. Thank you in advancearrow_forwardNet charge and isoelectric point of an amino acid with an ionizable side group.Consider the net charge and isoelectric point of an amino acid with ionizable side (R-) group.(a) Identify the acidic amino acid(s) capable of having a negatively charged carboxyl side group.(b) Identify the basic amino acid(s) capable of having a positively charged amino side group.(c) For an amino acid with a side (R-) chain that can ionize to a negative charge, derive a general expression in terms of measured pH and known pKa values of α-carboxyla-amino (pKca), α-amino(pKaa),and side group (pKRa), respectively, for the net charge of an amino acid Consider the net charge and isoelectric point of an amino acid with ionizable side (R-) group.(d) For an amino acid with a side (R-) chain that can ionize to a positive charge, derive a general expression in terms of measured pH and known pKa values ofα-carboxyl (pKca), α-amino (pKaa), and side group (pKRa), respectively, for the net charge of the amino acid.(e)…arrow_forward
- The pKa of the conjugate acid of guanidine is 13.6, making it one of thestrongest neutral organic bases. Offer an explanation.arrow_forwardComplete the table for the ionizable groups of the fictitious amino acid hypothetinine. Group alpha-amino alpha-carboxyl Ka 5.24 x 10-⁹ 2.13 x 10-3 pKa (to TWO decimals) 8.9 2.7 Average charge of group when pH=pK (to ONE decimal) -0.5 +0.5arrow_forwardDraw Tryptophan in a peptide bond. Explain all of the bonds using valence bond theory (VBT). Next, explain where VBT fails and how molecular orbital theory is a better description of key regions of this amino acid and the peptide bonds it forms with other residuesarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Chemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Introductory Chemistry: A FoundationChemistryISBN:9781337399425Author:Steven S. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
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
Introductory Chemistry: A Foundation
Chemistry
ISBN:9781337399425
Author:Steven S. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning