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 4.48AP
As we shall see in Chapter 19, hydrogens on a carbon adjacent to a carbonyl group are far more acidic than those not adjacent to a carbonyl group. The anion derived from acetone, for example, is more stable than is the anion derived from ethane. Account for the greater stability of the anion from acetone.
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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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- Answer 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_forwardOne structure for the conjugate acid of acetone is The electrons in the carbon–oxygen double bond are pushable electrons, and the atom is a receptor.arrow_forward
- List the following compounds by discussing their basicity.arrow_forwardRank the following in order of increasing acidity. (1 = least acidic ... 4 = most acidic)arrow_forwardWhich one of the following is NOT basic? OH- HPO4^2- NO3- SO4^2- ClO4- In the following reaction in aqueous solution, the acid reactant is __________, and its conjugate base product is __________. CH3NH2 + HSO4^- <–> CH3NH3^+ + SO4^2– CH3NH2; CH3NH3+ HSO4-; SO4^2- CH3NH2; SO4^2- HSO4-; H3O+ HSO4-; CH3NH3+ Three acids found in foods are lactic acid (in milk products), oxalic acid (in rhubarb), and malic acid (in apples). The pKa values are LA = 3.88, OA = 1.23, and MA = 3.40. Which list has the conjugate bases of these acids in order of decreasing strength? * Lactate > oxalate > malate Oxalate > Lactate > malate Oxalate > malate > lactate malate > lactate > Oxalate Lactate > malate > oxalatearrow_forward
- Which of the following is expected to be the strongest acid? a. H3PO4 b. H2CO3 c. HNO2 d. H2SO3arrow_forwardWhat is the sequence of the following to show an increasing strength of basicity? a. HNO2 b. HOC6H5 c. HSO4- d. HCNarrow_forwardUsing your knowledge of how molecular structure can influence acid strength, explain the following statements. H3AsO4 is a stronger acid than H3AsO3. H2Te is a stronger acid than H2O CH3CH2COOH is a stronger acid than CH3CH2CH2OHarrow_forward
- Rank the following acids in order from weakest acid to strongest acid. Explain why you ranked the acids in the designated order. Your answer should include, if applicable, reasons based in inductive effects, resonance (electron donating groups vs electron withdrawing groups), etc.arrow_forward1. For this acid-base reaction: C(-)H3 + H3O+ >>> CH4 +H2O, the conjugate acid of carbonian (C(-)H3) is 2. Complete the equation: HC(triple bond)N + NaOH >>> 3. Rank acidity of these from most acidic to least acidic: NH3, HF, H2O, NH3, NaHarrow_forwardRank these from strongest acid to weakest acidarrow_forward
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