Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Chapter 4, Problem 4.54AP
Following is a structural formula for imidazole, a building block of the essential amino acid histidine (Chapter 27). It is also a building block of histamine, a compound all too familiar to people with allergies and takers of antihistamines. When imidazole is dissolved in water, proton transfer to it gives a cation. Is this cation better represented by structure A or B? Explain.
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Chapter 4 Solutions
Organic Chemistry
Ch. 4.2 - For each conjugate acid-base pair, identify the...Ch. 4.2 - Write these reactions as proton-transfer...Ch. 4.2 - Following is a structural formula for guanidine,...Ch. 4.2 - Write an equation to show the proton transfer...Ch. 4.3 - For each value of Ka, calculate the corresponding...Ch. 4.4 - Predict the position of equilibrium and calculate...Ch. 4.5 - Calculate Keq for a reaction with G0 = 17.1 kJ/mol...Ch. 4.6 - Acid-Base Equilibria Many factors contribute to...Ch. 4.6 - What is the relative trend in acidity and pKa of...Ch. 4.7 - Write an equation for the reaction between each...
Ch. 4 - For each conjugate acid-base pair, identify the...Ch. 4 - Complete a net ionic equation for each...Ch. 4 - Arrange the compounds in each set in order of...Ch. 4 - Prob. 4.12PCh. 4 - In acetic acid, CH3COOH, the OH hydrogen is more...Ch. 4 - Which has the larger numerical value? (a) The pKa...Ch. 4 - In each pair, select the stronger acid. (a)...Ch. 4 - Arrange the compounds in each set in order of...Ch. 4 - Arrange the compounds in each set in order of...Ch. 4 - If the G for a reaction is 4.5 kcal/mol at 298 K,...Ch. 4 - Calculate the Keq for the following reactions from...Ch. 4 - Prob. 4.20PCh. 4 - Answer true or false to the following statements...Ch. 4 - In each of the following three reaction coordinate...Ch. 4 - The acid-base chemistry reaction of barium...Ch. 4 - Unless under pressure, carbonic acid (H2CO3) in...Ch. 4 - Prob. 4.25PCh. 4 - Acetic acid, CH3COOH, is a weak organic acid, pKa...Ch. 4 - Benzoic acid, C6H5COOH (pKa 4.19), is only...Ch. 4 - Prob. 4.28PCh. 4 - One way to determine the predominant species at...Ch. 4 - Will acetylene react with sodium hydride according...Ch. 4 - Prob. 4.31PCh. 4 - For each equation, label the Lewis acid and the...Ch. 4 - Complete the equation for the reaction between...Ch. 4 - Each of these reactions can be written as a Lewis...Ch. 4 - The sec-butyl cation can react as both a...Ch. 4 - Prob. 4.36APCh. 4 - Prob. 4.37APCh. 4 - Prob. 4.38APCh. 4 - Explain why the hydronium ion, H3O+, is the...Ch. 4 - What is the strongest base that can exist in...Ch. 4 - Prob. 4.42APCh. 4 - Prob. 4.43APCh. 4 - Methyl isocyanate, CH3N=C=O, is used in the...Ch. 4 - Offer an explanation for the following...Ch. 4 - Prob. 4.46APCh. 4 - Alcohols (Chapter 10) are weak organic acids, pKa...Ch. 4 - As we shall see in Chapter 19, hydrogens on a...Ch. 4 - 2,4-Pentanedione is a considerably stronger acid...Ch. 4 - Write an equation for the acid-base reaction...Ch. 4 - Prob. 4.51APCh. 4 - Prob. 4.52APCh. 4 - Prob. 4.53APCh. 4 - Following is a structural formula for imidazole, a...
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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
- The following reactions illustrate Brnsted acid-base behavior. Complete each equation. a.HI(aq)+?H3O+(aq)+I(aq) b.NH3(l)+?NH4++NH2 c.H2C2O4(aq)+H2O(l)?+HC2O4(aq) d.H2N2O2(aq)+H2O(l)H3O+(aq)+? e.?+H2O(l)H3O+(aq)+CO32(aq)arrow_forwardConsider the following four solutions: (1) apple juice, pH 3.8, (2) pickle juice, pH 3.5, (3) carbonated beverage, pH 3.0, and (4) drinking water, pH 7.2. a. Which solution has the highest [H3O+]? b. Which solution has the highest [OH]? c. List the solutions in order of increasing acidity. d. List the solutions in order of decreasing basicity.arrow_forwardHydrazine, N2H4 (having the structure H2NNH2), and its derivatives have been used as rocket fuels. Draw the Lewis electron-dot formula for the hydrazine molecule. Describe the geometries expected about the nitrogen atoms in this molecule. Why would you expect hydrazine to be basic? Which substance, NH3 or N2H4, would you expect to be more basic? Why? Write the chemical equation in which hydrazine reacts with hydrochloric acids to form the salt N2H5Cl. Consider the positive ion of this salt. How does its basic character compare with that of NH3 and N2H4? Explain.arrow_forward
- Using the diagrams shown in Problem 10-37, which of the four acids is the weakest acid?arrow_forwardIn each of the following acid-base reactions, identify the Brnsted acid and base on the left and their conjugate partners on the right. (a) C2H5N(aq) + CH3CO2H(aq) C5H5NH+(aq) + CH3CO2(aq) (b) N2H4(aq) + HSO4(aq) N2H5+(aq) + SO42(aq) (c) [Al(H2O)6]3+ (aq) + OH(aq) [Al(H2O)5OH]2+ (aq) + H2O+()arrow_forwardFor conjugate acidbase pairs, how are Ka and Kb related? Consider the reaction of acetic acid in water CH3CO2H(aq)+H2O(l)CH3CO2(aq)+H3O+(aq) where Ka = 1.8 105 a. Which two bases are competing for the proton? b. Which is the stronger base? c. In light of your answer to part b. why do we classify the acetate ion (CH3CO2) as a weak base? Use an appropriate reaction to justify your answer. In general, as base strength increases, conjugate acid strength decreases. Explain why the conjugate acid of the weak base NH3 is a weak acid. To summarize, the conjugate base of a weak acid is a weak base and the conjugate acid of a weak base is a weak acid (weak gives you weak). Assuming Ka for a monoprotic strong acid is 1 106, calculate Kb for the conjugate base of this strong acid. Why do conjugate bases of strong acids have no basic properties in water? List the conjugate bases of the six common strong acids. To tie it all together, some instructors have students think of Li+, K+, Rb+, Cs+, Ca2+, Sr2+, and Ba2+ as the conjugate acids of the strong bases LiOH, KOH. RbOH, CsOH, Ca(OH)2, Sr(OH)2, and Ba(OH)2. Although not technically correct, the conjugate acid strength of these cations is similar to the conjugate base strength of the strong acids. That is, these cations have no acidic properties in water; similarly, the conjugate bases of strong acids have no basic properties (strong gives you worthless). Fill in the blanks with the correct response. The conjugate base of a weak acid is a_____base. The conjugate acid of a weak base is a_____acid. The conjugate base of a strong acid is a_____base. The conjugate acid of a strong base is a_____ acid. (Hint: Weak gives you weak and strong gives you worthless.)arrow_forward
- Place the species in each of the following groups in order of increasing acid strength. a. H2O, H2S, H2Se (bond energies: HO, 467 kJ/mol; HS, 363 kJ/mol; HSe, 276 kJ/mol) b. CH3CO2H, FCH2CO2H, F2CHCO2H, F3CCO2H c. NH4+, HONH3+ d. NH4+, PH4+ (bond energies: NH, 391 kJ/mol; PH, 322 kJ/mol) Give reasons for the orders you chose.arrow_forwardWrite a chemical equation to describe the proton transfer that occurs when each of these acids is added to water. (a) HCO3 (b) HCl (c) CH3COOH (d) HCNarrow_forwardHow is acid strength related to the value of Ka? What is the difference between strong acids and weak acids (see Table 13-1)? As the strength of an acid increases, what happens to the strength of the conjugate base? How is base strength related to the value of Kb? As the strength of a base increases, what happens to the strength of the conjugate acid?arrow_forward
- Rank the compounds in each of the following groups in order of increasing acidity or basicity, as indicated, and explain the order you assign. (a) acidity: HCI, HBr, HI. (b)basicity: H2O, OH-, H-, CI-. (c) basicity: Mg(OH)2, Si(OH)4, ClO3(OH) (Hint: Formula could also be written as HCIO4). (d) acidity: HF, H2O, NH3, CH4arrow_forwardRank the following acids (M=0.10)in order of decreasing[ H+ ]: HFHCl HCN HCIOarrow_forward
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