Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 21, Problem 78P
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.)
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Find a molecular formula for these unknowns
(ME EX2) Prblms 8-11 Can you please explain problems 8 -11 to me in detail, step by step? Thank you so much! If needed color code them for me.
Don't used hand raiting
Chapter 21 Solutions
Organic Chemistry (8th Edition)
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
- The following 'H NMR spectrum was taken with a 750 MHz spectrometer: 1.0 0.5 0.0 10.0 9.0 8.0 7.0 6.0 5.0 4.0 3.0 ' 2.0 1.0 0.0 (ppm) What is the difference Av in the frequency of RF ac Δν ac radiation absorbed by the a and c protons? (Note: it's not equal to the difference in chemical shifts.) Round your answer to 2 significant digits, and be sure it has an appropriate unit symbol. = O O a will shift left, c will shift right. O a will shift right, c will shift left. a and c will both shift left, with more space between them. Suppose a new spectrum is taken with a 500 MHz spectrometer. What will be true about this new spectrum? O a and c will both shift left, with less space between them. O a and c will both shift right, with more space between them. O a and c will both shift right, with less space between them. Which protons have the largest energy gap between spin up and spin down states? O None of the above. ○ a Ob Explanation Check C Ar B 2025 McGraw Hill LLC. All Rights Reserved.…arrow_forwardWhat mass of Na2CO3 must you add to 125g of water to prepare 0.200 m Na2CO3? Calculate mole fraction of Na2CO3, mass percent, and molarity of the resulting solution. MM (g/mol): Na2CO3 105.99; water 18.02. Final solution density is 1.04 g/mL.arrow_forward(ME EX2) Prblms Can you please explain problems to me in detail, step by step? Thank you so much! If needed color code them for me.arrow_forward
- Experiment #8 Electrical conductivity & Electrolytes. Conductivity of solutions FLINN Scientific Scale RED LED Green LED LED Conductivity 0 OFF OFF 1 Dim OFF 2 medium OFF 3 Bright Dim Low or Nowe Low Medium High 4 Very Bright Medium nd very high AA Δ Δ Δ Δ Δ Δ Δ Δ Δ Δ Δ SE=Strong Electrolyte, FE = Fair Electrolyte CWE = Weak Electrolyte, NE= Noni Electrolyte, #Solutions 1 0.1 M NaCl 2/1x 102 M NaCl, 3/1X103 M Nall Can Prediction M Observed Conductivity Very bright red Bright red Dim red you help me understand how I'm supposed to find the predictions of the following solutions? I know this is an Ionic compound and that the more ions in a solution means it is able to carry a charge, right? AAAA Darrow_forward(SE EX 2) Prblsm 4-7: Can you please explain problems 4-7 and color code if needed for me. (step by step) detail explanationsarrow_forward(SE EX 2) Problems 8-11, can you please explain them to me in detail and color-code anything if necessary?arrow_forward
- (ME EX2) Problems 15-16 Could you please explain problems 15 through 16 to me in detail, step by step? Thank you so much! If necessary, please color-code them for me.arrow_forward1.)show any electrophilic aromatic substitution, identify the electriphile, nucleophile and transition statearrow_forward(SE EX 2) Problems 15-16, can you please explain them to me in detail and color-code anything if necessary?arrow_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
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Biomolecules - Protein - Amino acids; Author: Tutorials Point (India) Ltd.;https://www.youtube.com/watch?v=ySNVPDHJ0ek;License: Standard YouTube License, CC-BY