EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 22, Problem 33P
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 22 Solutions
EBK ORGANIC CHEMISTRY
Ch. 22.2 - Compare each of the mechanisms listed here with...Ch. 22.2 - Prob. 3PCh. 22.2 - Prob. 4PCh. 22.3 - a. Draw the mechanism for the following reaction...Ch. 22.5 - Prob. 7PCh. 22.5 - Propose a mechanism for the Co2+ catalyzed...Ch. 22.6 - Prob. 9PCh. 22.7 - Prob. 10PCh. 22.7 - Prob. 12PCh. 22.7 - Prob. 13P
Ch. 22.9 - Which of the following amino acid side chains can...Ch. 22.9 - Which of the following C-terminal peptide bonds is...Ch. 22.9 - Carboxypeptidase A has esterase activity as well...Ch. 22.10 - Arginine and lysine side chains fit into trypsins...Ch. 22.10 - Explain why serine proteases do not catalyze...Ch. 22.11 - If H2 18O is used in the hydrolysis reaction...Ch. 22.11 - Draw the pH-activity profile for an enzyme that...Ch. 22.12 - The pHactivity profile for glucose-6-phosphate...Ch. 22.12 - Prob. 23PCh. 22.13 - Draw the mechanism for the hydroxide ion-catalyzed...Ch. 22.13 - What advantage does the enzyme gain by forming an...Ch. 22.13 - Prob. 26PCh. 22.13 - Prob. 27PCh. 22.13 - Aldolase shows no activity if it is incubated with...Ch. 22 - Which of the following parameters would be...Ch. 22 - Prob. 29PCh. 22 - Prob. 30PCh. 22 - Prob. 31PCh. 22 - Indicate the type of catalysis that is occurring...Ch. 22 - The deuterium kinetic isotope effect (KH2O/KD2O)...Ch. 22 - Prob. 34PCh. 22 - Co2+ catalyzes the hydrolysis of the lactam shown...Ch. 22 - there are two kinds of aldolases. Class I...Ch. 22 - Prob. 37PCh. 22 - The hydrolysis of the ester shown here is...Ch. 22 - Prob. 39PCh. 22 - At pH = 12, the rate of hydrolysis of ester A is...Ch. 22 - 2-Acetoxycyclohexyl tosylate reacts with acetate...Ch. 22 - Proof that an imine was formed between aldolase...Ch. 22 - Prob. 43PCh. 22 - a. Explain why the alkyl halide shown here reacts...Ch. 22 - Triosephosphate isomerase (TIM) catalyzes the...
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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
- Write the chemical equation for the reaction of N,N-diethyl-1-propanamine with water. Which is the formula of this rule of reaction? (Hint: the amine is a base):arrow_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_forward4. Using structures for all species, write the complete esterification reaction begun below: HSO, methanol (CH3OH) + salicylic acidarrow_forward
- Physical 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_forwardExplain the effect of the pH on the protonation of the functional groups present in ascorbic acid (C6H8O6) and citric acid (C6H8O7).arrow_forward
- The amount of tartaric acid is responsible for the tartness of wine and controls the acidity of the wine. Tartaric acid also plays a very significant role in the overall taste, feel and color of a wine. Tartaric acid is a diprotic organic acid The chemical formula for tartaric acid is C4H6O6 and its structural formula is HO2CCH(OH)CH(OH)CO2H. A 50.00 mL sample of a white dinner wine required 21.48 mL of 0.03776 M NaOH to achieve a faint pink color. Express the acidity of the wine in terms of grams of tartaric acid, H2C4H4O6 (M. M. = 150.10) per 100 mL of wine. Assume that the two acidic hydrogens are titrated at the end point. MM H2C4H4O6 = 150.10 MM NaOH = 40.00 Below is the balanced chemical equation for this titration.arrow_forwardCarboxylic acid is not the answerarrow_forwardAn 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_forward
- propanoic acid + methanol (in concentrated sulfuric acid)arrow_forward¨ What other types of analgesics are on the market? How does their action compare with aspirin and why are these alternative drugs necessary? Discuss the differences among the following compounds by drawing their structures: Acetylsalicylic acid, Acetaminophen (Paracetamol), Ibuprofen, Paracetamol and Phenacetin.arrow_forwardFind the structural formulas for salicylic acid, acetic anhydride, and aspirin. Use these structural formulas to construct a reaction equation describing the synthesis of aspirin. (CH3CO)2O + HOC6H4COOH → CH3CO2C6H4CO2H + CH3COOH acetic anhydride salicylic acid acetylsalicylic acid acetic acid Part I Synthesis of Aspirin Mass of salicylic acid used (g) 2.029g Volume of acetic anhydride used (mL) 5ml Mass of acetic anhydride used (vol. × 1.08 g/mL) 5.4g Mass of aspirin synthesized (g) 3.256g Part II Melting Temperature Data Melting temperature (°C) 133°C Part III Salicylic Acid Standard Stock Solution Initial mass of salicylic acid (g) 0.210g Moles of salicylic acid (mol) 0.0147 mol Initial molarity of salicylic acid (M) 0.724 M Part III Beer’s Law Data for Salicylic Acid Standard Solutions Trial Concentration (M) Absorbance Water (mL) 1 10 0.301 0…arrow_forward
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