Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Chapter 23, Problem 34P
The deuterium kinetic isotope effect (KH2O/KD2O) for the hydrolysis of aspirin is 2.2. What does this tell you about the kind of catalysis exerted by the ortho-carboxyl substituent? (Hint: It is easier to break an O — H bond than an O — D bond.)
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Chapter 23 Solutions
Organic Chemistry
Ch. 23.2 - Compare each of the mechanisms listed here with...Ch. 23.2 - Prob. 3PCh. 23.2 - Prob. 4PCh. 23.3 - a. Draw the mechanism for the following reaction...Ch. 23.5 - Prob. 7PCh. 23.5 - Propose a mechanism for the Co2+ catalyzed...Ch. 23.6 - Prob. 9PCh. 23.7 - Prob. 10PCh. 23.7 - Prob. 12PCh. 23.7 - Prob. 13P
Ch. 23.9 - Which of the following amino acid side chains can...Ch. 23.9 - Which of the following C-terminal peptide bonds is...Ch. 23.9 - Carboxypeptidase A has esterase activity as well...Ch. 23.9 - Arginine and lysine side chains fit into trypsins...Ch. 23.9 - Explain why serine proteases do not catalyze...Ch. 23.10 - If H2 18O is used in the hydrolysis reaction...Ch. 23.10 - When apples that have been cut are exposed to...Ch. 23.11 - Prob. 22PCh. 23.11 - The pHactivity profile for glucose-6-phosphate...Ch. 23.11 - Draw the pH-activity profile for an enzyme that...Ch. 23.12 - Prob. 25PCh. 23.12 - Draw the mechanism for the hydroxide ion-catalyzed...Ch. 23.12 - What advantage does the enzyme gain by forming an...Ch. 23.12 - Prob. 28PCh. 23.12 - Aldolase shows no activity if it is incubated with...Ch. 23 - Which of the following parameters would be...Ch. 23 - Prob. 30PCh. 23 - Prob. 31PCh. 23 - Prob. 32PCh. 23 - Indicate the type of catalysis that is occurring...Ch. 23 - The deuterium kinetic isotope effect (KH2O/KD2O)...Ch. 23 - Prob. 35PCh. 23 - Co2+ catalyzes the hydrolysis of the lactam shown...Ch. 23 - there are two kinds of aldolases. Class I...Ch. 23 - Prob. 38PCh. 23 - The hydrolysis of the ester shown here is...Ch. 23 - Prob. 40PCh. 23 - At pH = 12, the rate of hydrolysis of ester A is...Ch. 23 - 2-Acetoxycyclohexyl tosylate reacts with acetate...Ch. 23 - Proof that an imine was formed between aldolase...Ch. 23 - Prob. 44PCh. 23 - a. Explain why the alkyl halide shown here reacts...Ch. 23 - Triosephosphate isomerase (TIM) catalyzes the...
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- Write an equation for the reaction of chloroacetic acid (Ka=1.5103) with trimethylamine (Kb=5.9105) . Calculate the equilibrium constant for the reaction. If 0.10 M solutions of these two species are mixed, what will be their concentrations at equilibrium?arrow_forwardPAP Chemistry-2903012-42100P-1/ Le Chatelier's Principle/ Lesson 128 2. Zinc (Zn) granules react slowly with dilute hydrochloric acid (HCI), but much faster if the acid is concentrated. Zn(s) 2HCI(aq)ZnCl2(aq) + H2(g) Zinc + Hydrochloric Acid Zinc Chloride + Hydrogen What causes the reaction to proceed faster with concentrated acid? The concentrated hydrochloric acid causes more hydrogen gas to be produced. The pressure of hydrogen gas molecules increases as concentration increases. The concentrated hydrochloric acid molecules move faster than in dilute acid. There are more collisions between the zinc and concentrated hydrochloric acid. PREVIOUarrow_forwardWhy does the dehydration of an alcohol more often use concentrated sulfuric acid, H2SO4H2SO4, as the acid catalyst rather than dilute hydrochloric acid, HCl? Select one or more: Hydrochloric acid is too small to effectively react with the alcohol in the reaction. The additional water solvent from a dilute solution could reverse the dehydration reaction. Only acids with more than one proton can complete the dehydration reaction. The presence of the chloride ion could result in a competing substitution reaction.arrow_forward
- 4. Using structures for all species, write the complete esterification reaction begun below: HSO, methanol (CH3OH) + salicylic acidarrow_forwardPhysical and chemical similarities and differences of methyl cinnamate C10H10O2 and Aspirin (acetylsalicylic acid) C9H8O4 ?arrow_forwardWrite the IUPAC name of the compound produced by this reaction: O + B₁₂ 1.arrow_forward
- Methyl benzoate can be synthesized by a Fisher Esterification reaction, and then this ester can be used as a starting material in the grignard synthesis of triphenyl carbinol. Suppose that in the synthesis of methyl benzoate, a student started with 12 grams of benzoic acid and 29.86 ml of methanol. After finishing the preparation of the ester, 7.63 grams of methylbenzoate was obtained, and the benzoic acid reacted completely. What is the percent yield of the ester? ( density methanol = 0.791 g/ml, methanol = 32.04 g/mol, methyl benzoate = 136.15 g/mol, benzoic acid = 122.12 g/mol )arrow_forwardEnumerate the uses of esters in pharmacy. What is the purpose of adding concentrated sulfuric acid and heating the mixture? What was the purpose of sodium bicarbonate and sodium chloride solutions in the synthesis of esters?arrow_forwardExplain the effect of the pH on the protonation of the functional groups present in ascorbic acid (C6H8O6) and citric acid (C6H8O7).arrow_forward
- An acetylation mixture containing 3.5 g acetic anhydride is reacted with 4.5 g salicylic acid. The experimental yield of the reaction is 5.1 g. What is the percentage yield of the reaction? To help you, here are the molar masses: Acetic anhydride (C4H6O3): 102.1 g·mol-1 Salicylic acid (C7H6O3): 138.1 g·mol-1arrow_forwardWhich of the following compounds has a different classification according to their solubility? ac NH₂ НО. HS OH OH OH NH₂ Farrow_forwardWhat is the purpose of the concentrated sulfuric acid in the preparation of aspirin?arrow_forward
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