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 4.32P
For each equation, label the Lewis acid and the Lewis base. In addition, show all unshared pairs of electrons on the reacting atoms and use curved arrows to show the flow of electrons in each reaction.
- (a) F– + BF3 → BF4–
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Why is HCl so acidic?
For example, why is H-Cl more acidic than H-S-CH3?
Isn't the conjugate base's negative charge more stabilized with a sulfur and extra methyl group (by the induction effect)? While Cl is more electronegative than Sulfur, I would assume Cl being alone as its own ion would make it less stable.
As we will see in later chapters, many steps in key reaction sequences involve acid–base reactions. (a) Draw curved arrows to illustrate the flow of electrons in steps [1]–[3]. (b) Identify the base and its conjugate acid in step [1]. (c) Identify the acid and its conjugate base in step [3].
For the following reaction, draw the Lewis Dot structure for each reactant and product including any formal charges. Also identify the Lewis Acid and the Lewis Base for this reaction.
CH3CH2CCH + NH2- -> CH3CH2CC- + NH3
On the product side of the equation, one of the C atoms has 1 unshared pair of electrons and is (-) charged.
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_forwardAnswer true or false to the following statements about the mechanism of acid-base reactions. (a) The acid and base must encounter each other by a collision in order for the proton to transfer. (b) All collisions between acids and bases result in proton transfer. (c) During an acid-base reaction the lone pair on the base fills the A-H antibonding sigma orbital.arrow_forwardComplete the equation for the reaction between each Lewis acid-base pair. In each equation, label which starting material is the Lewis acid and which is the Lewis base; use curved arrows to show the flow of electrons in each reaction. In doing this problem, it is essential that you show valence electrons for all atoms participating in each reaction. (a) (b) (c) (d)arrow_forward
- Several acids and their respective equilibrium constants are: Which is the strongest acid? Which is the weakest acid? Which acid has the weakest conjugate base? Which acid has the strongest conjugate base?arrow_forward(a) Given that Ka for acetic acid is 1.8 x 10-5 and that forhypochlorous acid is 3.0 x 10-8, which is the stronger acid?(b) Which is the stronger base, the acetate ion or the hypochloriteion? (c) Calculate Kb values for CH3COO- and ClO-.arrow_forwardLabel the Lewis acid and Lewis base in each reaction. Use curved arrowsto show the movement of electron pairs.arrow_forward
- Rank the following Brønsted–Lowry acids in order of increasing acidity. Which compound forms the strongest conjugate base?arrow_forwardAs we will see in later chapters, many steps in key reaction sequencesinvolve acid–base reactions. (a) Draw curved arrows to illustrate the flow of electrons in steps [1]–[3]. (b) Identify the base and its conjugate acid in step [1]. (c) Identify the acid and its conjugate base in step [3].arrow_forwardWhich of the following two acids has the stronger conjugate base? Nitrous acid, Ka = 7.1 x 10–4 Phenol, Ka = 1.0 x 10–10 The strength of the conjugate base cannot be obtained from the information given. Nitrous acid, because it has a larger Ka value. Nitrous acid, because it has a smaller Ka value. Phenol, because it has a larger Ka value. Phenol, because it has a smaller Ka value.arrow_forward
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