Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 22.1, Problem 1P
- a. Explain why, when the imidazole ring of histidine is protonated, the double-bonded nitrogen is the nitrogen that accepts the proton.
- b. Explain why. when the guanidino group of arginine is protonated, the double-bonded nitrogen is the nitrogen that accepts the proton.
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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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- Identify the starting material in the following reaction. Click the "draw structure" button to launch the drawing utility. draw structure ... [1] 0 3 C10H18 [2] CH3SCH3 Harrow_forwardIn an equilibrium mixture of the formation of ammonia from nitrogen and hydrogen, it is found that PNH3 = 0.147 atm, PN2 = 1.41 atm and Pн2 = 6.00 atm. Evaluate Kp and Kc at 500 °C. 2 NH3 (g) N2 (g) + 3 H₂ (g) K₂ = (PN2)(PH2)³ = (1.41) (6.00)³ = 1.41 x 104arrow_forwardWhat alkene or alkyne yields the following products after oxidative cleavage with ozone? Click the "draw structure" button to launch the drawing utility. and two equivalents of CH2=O draw structure ...arrow_forward
- H-Br Energy 1) Draw the step-by-step mechanism by which 3-methylbut-1-ene is converted into 2-bromo-2-methylbutane. 2) Sketch a reaction coordinate diagram that shows how the internal energy (Y- axis) of the reacting species change from reactants to intermediate(s) to product. Brarrow_forward2. Draw the missing structure(s) in each of the following reactions. The missing structure(s) can be a starting material or the major reaction product(s). C5H10 H-CI CH2Cl2 CIarrow_forwardDraw the products of the stronger acid protonating the other reactant. དའི་སྐད”“ H3C OH H3C CH CH3 KEq Product acid Product basearrow_forward
- Draw the products of the stronger acid protonating the other reactant. H3C NH2 NH2 KEq H3C-CH₂ 1. Product acid Product basearrow_forwardWhat alkene or alkyne yields the following products after oxidative cleavage with ozone? Click the "draw structure" button to launch the drawing utility. draw structure ... andarrow_forwardDraw the products of the stronger acid protonating the other reactant. H3C-C=C-4 NH2 KEq CH H3C `CH3 Product acid Product basearrow_forward
- 2. Draw the missing structure(s) in each of the following reactions. The missing structure(s) can be a starting material or the major reaction product(s). C5H10 Br H-Br CH2Cl2 + enant.arrow_forwardDraw the products of the stronger acid protonating the other reactant. KEq H₂C-O-H H3C OH Product acid Product basearrow_forwardDraw the products of the stronger acid protonating the other reactant. OH KEq CH H3C H3C `CH3 Product acid Product basearrow_forward
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