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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Textbook Question
Chapter 4, Problem 4.35AP
The sec-butyl cation can react as both a Brønsted-Lowry acid (a proton donor) and a Lewis acid (an electron pair acceptor) in the presence of a water–sulfuric acid mixture. In each case, however, the product is different. The two reactions are as follows:
- (a) In which reaction(s) does this cation react as a Lewis acid? In which reaction(s) does it react as a Brønsted-Lowry acid?
- (b) Write Lewis structures for reactants and products and show by the use of curved arrows how each reaction occurs.
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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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- Complete a net ionic equation for each proton-transfer reaction using curved arrows to show the flow of electron pairs in each reaction. In addition, write Lewis structures for all starting materials and products. Label the original acid and its conjugate base; label the original base and its conjugate acid. If you are uncertain about which substance in each equation is the proton donor, refer to Table 4.1 for the relative strengths of proton acids. (a) NH3+HCl (b) CH3CH2O+HCl (c) HCO3+OH (d) CH3COO+NH4+arrow_forwardHypofluorous acid, HOF, is known, but fluorous acid, HOFO, is not. Which acid would you expect to be stronger?arrow_forwardIn the following net ionic reaction, identify each species as either a Brnsted-Lowry acid or a Brnsted -Lowry base: CH3COO(aq)+HS(aq)CH3COOH(aq)+S2(aq). Identify the conjugate of each reactant and state whether it is a conjugate acid or a conjugate base.arrow_forward
- 1. Which of the following can act as a Lewis acid? (Hint : In each case, draw the Lewis electron dot structure of the molecule or ion. Are there lone pairs of electrons on the central atom? If so, it can be a Lewis base. Does the central atom lack an electron pair? If so, it can behave as a Lewis acid.) PH3 BCl3 H2S HS−arrow_forwardFor oxyacids, how does acid strength depend on a. the strength of the bond to the acidic hydrogen atom? b. the electronegativity of the element bonded to the oxygen atom that bears the acidic hydrogen? c. the number of oxygen atoms? How does the strength of a conjugate base depend on these factors? What type of solution forms when a nonmetal oxide dissolves in water? Give an example of such an oxide. What type of solution forms when a metal oxide dissolves in water? Give an example of such an oxide.arrow_forwarda Write a net ionic equation to show that hypochlorous acid behaves as a Brnsted-Lowry acid in water. b The substance triethanolamine is a weak nitrogen-containing base, like ammonia. Write a net ionic equation to show that triethanolamine, C6H15O3N, behaves as a Brnsted-Lowry base in water.arrow_forward
- Aluminum chloride, AlCl3, behaves more as a molecular compound than an ionic one. This is illustrated in its ability to form a fourth covalent bond with a chloride ion: AlCl3+ClAlCl4. From the Lewis diagram of the aluminum chloride molecule and the electron configuration of the chloride ion, show that this is an acidbase reaction in the Lewis sense, and identify the Lewis acid and the Lewis base. Aluminum chloride is a white solid at room conditions, although it is typically manufactured mixed with some yellow ironIII chloride. Its appearance is that of an ionic compound.arrow_forwardCoal and other fossil fuels usually contain sulfur compounds that produce sulfur dioxide, SO2, when burned. One possible way to remove the sulfur dioxide is to pass the combustion gases into a tower packed with calcium oxide, CaO. Write the equation for the reaction. Identify each reactant as either a Lewis acid or a Lewis base. Explain how you arrived at your answer.arrow_forwardWrite balanced molecular equations to illustrate the following characteristic reactions of acids, using nitric acid (HNO3). a. Reaction with water to form hydronium ions b. Reaction with the solid oxide CaO c. Reaction with the solid hydroxide Mg(OH)2 d. Reaction with the solid carbonate CuCO3 e. Reaction with the solid bicarbonate KHCO3 f. Reaction with Mg metalarrow_forward
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