EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 21.3, Problem 5P
Interpretation Introduction
Interpretation:
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
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...
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- Tyrosine is a triprotic weak acid, with pKa1=2.41, pKa2=8.67, and pKa3=11.01. a) calculate the final [OH-] of a solution that starts with .3OM of the fully basic form. Do not assume the concentration of base is constant. b) at what pH range(s) would tyrosine act best as a buffer? c) calculate the pH of a solution at equilibrium which started with 0.043M at the monoprotonated H2A- form *Please show all work and not just answers, I'm looking to understand how to solve problems like these! TIAarrow_forwardA 1.00-mg sample of a pure protein yielded on hydrolysis 0.0165 mg of leucine and 0.0248 mg of isoleucine. What is the minimum possible molar mass of the protein? (MMleucine=MMisoleucine=131g/mol)arrow_forwardFor alanine, Ka1=5.1105,Ka2=1.81010 . Calculate the ratios [Z]/[C+] and [Z]/[A+] at pH (a) 2.00. (b) 6.00. (c) 10.50. What is the principal species at each pH?arrow_forward
- Can you please answer sub questions A and B and show all of the steps please and thank youarrow_forward[Review Topics] [References] Draw a structural formula for the major ionic form of the amino acid shown below when in aqueous solution at pH 1.5. . O H₂NCH₂COH 0- You do not have to consider stereochemistry. You do not have to explicitly draw Hatoms. Do not include lone pairs in your answer. They will not be considered in the grading. VI/@ 81 ///// 262 As 000. [Farrow_forwardE. E 4. Which chemical bond labeled in the structure below is called a peptide bond A. A; B. B; C. C; B D. D; A R1 H HIN E Н NIH D H C R2arrow_forward
- Ll.106.arrow_forwardGive detailed Solution with explanation (no need Handwrittenarrow_forwardSelect the correct representation of this aminoacid in aqueous solution at the stated pH values. pKa (a-CO₂H) = 2.20 pK₂ (α-NH₂) = 9.11 pKa (side chain OH) = 10.07 pl = 5.63 HO Lont out on on OH OH NH₂ NH₂ NH₁ HO NH₂ B D at pH 1 HO NH₂ of of an OH NH₂ NH₂ NH3 O E F G at pH 9.59 at pH 13. at pH 5.63 (the isoelectric point) HO OH HO [Choose ] [Choose ] [Choose ] [Choose ] an NH3 H OHarrow_forward
- Answer fastly, no need long explanation.arrow_forwardThe maximum number of amino acid side chains that can potentially form an ionic bond (+lIE- interaction) with the side chain of His is _at pH 21;at pH 7 and_at pH 11.5 andat pH 13.5. (assume no partial charges, only +/- whole number integers) 00: 2; 3:1 01:2:4:1 O2:2;3;0 00:2;3:0 00:2, 4:0 00:0: 2: 2 O none of thesearrow_forwardAnswer the following questions on the basis of the free energies of formation at 25°C shown in the table at the top of the next page: (a) Does the peptide bond between alanine and glycine form spontaneously under standard conditions?arrow_forward
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