EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Textbook Question
Chapter 21.6, Problem 22P
What amino acid is formed using the N-phthalimidomalonic ester synthesis when the following
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What hydrolysis products are formed when the attached compound istreated with aqueous acid ?
what would the strucutres look like for the following?
hexanoate reacys with methyl
hexanoate reacts with ethyl
butyrate reacts with ethyl
hexanoate reacts with 2-propyl
Which of the following is the most active acyl compound in terms of susceptibility to react?
A. ethylacetateB. acetamideC. acetic anhydrideD. acetyl chlorideE. acetic acid
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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- Some penicillins cannot be administered orally because their B-lactam is rapidly hydrolyzed by the acidic environment of the stomach. Draw the product that forms in the following hydrolysis reaction. нн N. R. но エーZarrow_forwardWhat is the difference between the aminolysis of an ester and that of an acyl halide?arrow_forwardWhen aspirin is made from acetic acid, the by product is H2O; when acetic anhydride 1Sused, the by-product is acetic acid. When acetyl chloride is used (see above), the by product is HC1. Which route should you use if you were working for Leica, a company that mass produces aspirin on a daily basis? Why?arrow_forward
- 5. Make the following via acetoacetic ester synthesis. شد کاarrow_forwardProstaglandins are a class of eicosanoids, fatty acid derivatives with a variety of extremely potent actions on vertebrate tissues. They are responsible for producing fever and inflammation and its associated pain. Prostaglandins are derived from the 20- carbon fatty acid arachidonic acid in a reaction catalyzed by the enzyme prostaglandin endoperoxide synthase. This enzyme, a cyclooxygenase, uses oxygen to convert arachidonic acid to PGG2, the immediate precursor of many different prostaglandins. Rate of formation of PGG2 with 10 mg/ml ibuprofen (mM/min) Arachidonic acid (mM) Rate of formation of PGG2 (mM/min) 0.190 12.3 0.228 13.9 0.342 17.5 0.570 1.33 22.2 28.8 7.71 8.88 11.9 16.3 24.0 The kinetic data given in the table are for the reaction catalyzed by a mutant of prostaglandin endoperoxide synthase. Focusing here on the first two columns, determine the Vmax and Km of the enzyme. Vmax Km = mM/min mMarrow_forward1. Amides are comparably unreactive to nucleophilic acyl substitution, yet the B-lactam antibiotics shown) are reactive with a hydroxyl group side chain of an amino acid. Why? R HOarrow_forward
- Which of the following is the most active acyl compound in terms of susceptibility to react? A. acetic acid B. acetic anhydride C. acetyl chloride D. acetamide E. ethylacetatearrow_forwardDuring the Panacetin separation lab, the ester of aspirin was hydrolyzed to the phenol. Based on the conditions in the Panacetin procedure, which of the following reactions could reasonably produced the hydrolyzed aspirin as a part of the separation ? Ester reduction Aminolysis of an ester Saponification of an ester with NaOH Acid-catalyzed ester hydrolysisarrow_forwardWhy is the ester hydrolysis slow in the beginning and becomes faster after sometime.arrow_forward
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