Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 22, Problem 72P
Propose a mechanism for the rearrangement of the thiazoline obtained from the reaction of Ed man's reagent with a peptide to a PTH-amino acid (page 1014). (Hint: Thioesters are very reactive toward nucleophiles.)
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Chapter 22 Solutions
Organic Chemistry
Ch. 22.1 - a. Explain why, when the imidazole ring of...Ch. 22.2 - a. Which isomer(R)-alanine or (S)-alanineis...Ch. 22.2 - Prob. 4PCh. 22.3 - Prob. 5PCh. 22.3 - Prob. 6PCh. 22.3 - Draw the predominant form for glutamate in a...Ch. 22.3 - a. Why is the pKa of the glutamate side chain...Ch. 22.4 - Explain why the pI of lysine is the average of the...Ch. 22.4 - Calculate the pI of each of the following amino...Ch. 22.4 - a. Which amino acid has the lowest pI value? b....
Ch. 22.4 - Prob. 13PCh. 22.5 - What aldehyde is formed when valine is treated...Ch. 22.5 - Prob. 15PCh. 22.5 - Prob. 16PCh. 22.5 - Prob. 17PCh. 22.5 - Prob. 18PCh. 22.6 - Why is excess ammonia used in the preceding...Ch. 22.6 - Prob. 20PCh. 22.6 - What amino acid is formed using the...Ch. 22.6 - Prob. 22PCh. 22.6 - What amino acid is formed when the aldehyde used...Ch. 22.7 - Esterase is an enzyme that catalyzes the...Ch. 22.8 - Draw the tetrapeptide Ala-Thr-Asp-Asn and indicate...Ch. 22.8 - Prob. 26PCh. 22.8 - Prob. 27PCh. 22.8 - Which bonds in the backbone of a peptide can...Ch. 22.9 - What is the configuration about each of the...Ch. 22.9 - Glutathione is a tripeptide whose function is to...Ch. 22.10 - What dipeptides would be formed by heating a...Ch. 22.10 - Suppose you are trying to synthesize the dipeptide...Ch. 22.10 - Show the steps in the synthesis of the...Ch. 22.10 - a. Calculate the overall yield of bradykinin when...Ch. 22.11 - Show the steps in the synthesis of the...Ch. 22.13 - Prob. 36PCh. 22.13 - In determining the primary structure of insulin,...Ch. 22.13 - A decapeptide undergoes partial hydrolysis to give...Ch. 22.13 - Explain why cyanogen bromide does not cleave on...Ch. 22.13 - Indicate the peptides produced from cleavage by...Ch. 22.13 - Prob. 42PCh. 22.13 - Three peptides were obtained from a trypsin...Ch. 22.14 - Prob. 44PCh. 22.15 - How would a protein that resides in the nonpolar...Ch. 22.16 - a. Which would have the greatest percentage of...Ch. 22 - Prob. 47PCh. 22 - Glycine has pK2 values of 2.34 and 9.60. At what...Ch. 22 - Prob. 49PCh. 22 - Prob. 50PCh. 22 - Aspartame (its structure is on page 1007) has a pl...Ch. 22 - Draw the form of aspartate that predominates at...Ch. 22 - A professor was preparing a manuscript for...Ch. 22 - Prob. 54PCh. 22 - Determine the amino acid sequence of a polypeptide...Ch. 22 - Prob. 56PCh. 22 - Which is the more effective buffer at...Ch. 22 - Identify the location and type of charge on the...Ch. 22 - Draw the product obtained when a lysine side chain...Ch. 22 - After the polypeptide shown below was treated with...Ch. 22 - Treatment of a polypeptide with 2-mercaptoethanol...Ch. 22 - Show how aspartame can be synthesized using DCCD.Ch. 22 - -Amino acids can be prepared by treating an...Ch. 22 - Reaction of a polypeptide with carboxypeptidase A...Ch. 22 - a. How many different octapeptides can be made...Ch. 22 - Glycine has pKa values of 2.3 and 9.6. Do you...Ch. 22 - A mixture of 15 amino acids gave the fingerprint...Ch. 22 - Write the mechanism for the reaction of an amino...Ch. 22 - Prob. 69PCh. 22 - Show how valine can be prepared by a. a...Ch. 22 - A chemist wanted to test his hypothesis that the...Ch. 22 - Propose a mechanism for the rearrangement of the...Ch. 22 - A normal polypeptide and a mutant of the...Ch. 22 - Determine the amino acid sequence of a polypeptide...
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- Using the conditions of spontaneity to deduce the signs of AH and AS Use the observations about each chemical reaction in the table below to decide the sign (positive or negative) of the reaction enthalpy AH and reaction entropy AS. Note: if you have not been given enough information to decide a sign, select the "unknown" option. reaction observations conclusions A The reverse of this reaction is always spontaneous but proceeds faster at temperatures above -48. °C. ΔΗ is (pick one) ✓ AS is (pick one) B This reaction is spontaneous except below 114. °C but proceeds at a slower rate below 135. °C. ΔΗ is (pick one) AS is (pick one) ΔΗ is C This reaction is exothermic and proceeds faster at temperatures above -43. °C. (pick one) AS is (pick one) v Х 5 ? 18 Ararrow_forwardion. A student proposes the following Lewis structure for the perchlorate (CIO) io : :0: : Cl : - - : :0: ك Assign a formal charge to each atom in the student's Lewis structure. atom central O formal charge ☐ top O ☐ right O ☐ bottom O ☐ Cl ☐arrow_forwardDecide whether these proposed Lewis structures are reasonable. proposed Lewis structure Yes. Is the proposed Lewis structure reasonable? Cl- : 2: :Z: :Z: N—N : 0: C C1: O CO No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* ☐ Yes. No, it has the wrong number of valence electrons. The correct number is: ☐ No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* | Yes. No, it has the wrong number of valence electrons. The correct number is: No, it has the right number of valence electrons but doesn't satisfy the octet rule. The symbols of the problem atoms are:* | If two or more atoms of the same element don't satisfy the octet rule, just enter the chemical symbol as many times as necessary. For example, if two oxygen atoms don't satisfy the octet rule, enter "0,0". ☑arrow_forward
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