Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 2.7, Problem 2.10P
Write equations for the following acid-base reactions Use the information in Table 2-2 or Appendix 4 to predict whether the equilibrium will favor the reactants or the products.
- a. HCOOH + −CN
- b. CH3COO− + CH3OH
- c. (CH3)2CHOH + NaNH2
- d. NaOCH3 + HCN
- e. HCI + CH3CH2OH
- f. H3O+ + CH3O−
SOLUTION
to (a): Cyanide is the conjugate base of HCN. It can accept a proton from formic acid:
Reading from Table 2-2 formic acid (pKa = 3.76) is a stronger acid than HCN (pKa = 9 22), and cyanide is a stronger base than formate. The products (weaker acid and base) are favored.
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Chapter 2 Solutions
Organic Chemistry (9th Edition)
Ch. 2.1A - Prob. 2.1PCh. 2.1B - The NF bond is more polar than the NH bond: but...Ch. 2.1B - For each of the following compounds 1. Draw the...Ch. 2.1B - Two isomers of 1,2-dichloroethene are known One...Ch. 2.2C - Prob. 2.5PCh. 2.2C - Prob. 2.6PCh. 2.3 - Prob. 2.7PCh. 2.4 - Calculate the pH of the following solutions a....Ch. 2.6A - Ammonia appears in Table 2-2 as both an acid and a...Ch. 2.7 - Write equations for the following acid-base...
Ch. 2.7 - Ethanol, methylamine. and acetic acid are all...Ch. 2.8 - Prob. 2.12PCh. 2.10 - Write equations for the following acid-base...Ch. 2.10 - Rank the following acids in decreasing order of...Ch. 2.11 - Prob. 2.15PCh. 2.11 - Prob. 2.16PCh. 2.11 - Consider each pair of bases and explain which one...Ch. 2.12 - Which is a stronger base ethoxide ion or acetate...Ch. 2.12 - Prob. 2.19PCh. 2.12 - Prob. 2.20PCh. 2.12 - Prob. 2.21PCh. 2.12 - Choose the more basic member of each pair of...Ch. 2.14 - Prob. 2.23PCh. 2.15D - Classify the following hydrocarbons and draw a...Ch. 2.16D - Prob. 2.25PCh. 2.17C - Draw a Lewis structure and classify each of the...Ch. 2.17C - Circle the functional groups in the following...Ch. 2 - The CN triple bond in acetonitrile has a dipole...Ch. 2 - Prob. 2.29SPCh. 2 - Sulfur dioxide has a dipole moment of 1.60 D....Ch. 2 - Which of the following pure compounds can form...Ch. 2 - Predict which member of each pair is more soluble...Ch. 2 - Prob. 2.33SPCh. 2 - Prob. 2.34SPCh. 2 - Predict which compound in each pair has the higher...Ch. 2 - All of the following compounds can react as acids...Ch. 2 - Rank the following species in order of increasing...Ch. 2 - Rank the following species in order of increasing...Ch. 2 - The Ka of phenylacetic acid is 5 2 105, and the...Ch. 2 - The following compound can become protonated on...Ch. 2 - The following compounds are listed in increasing...Ch. 2 - Prob. 2.42SPCh. 2 - Prob. 2.43SPCh. 2 - Compare the relative acidity of 1-molar aqueous...Ch. 2 - The following compounds can all react as acids. a....Ch. 2 - The following compounds can all react as bases. a....Ch. 2 - The following compounds can all react as acids. a....Ch. 2 - Prob. 2.48SPCh. 2 - Methyllithium (CH3Li) is often used as a base in...Ch. 2 - Label the reactants in these acid-base reactions...Ch. 2 - In each reaction, label the reactants as Lewis...Ch. 2 - Prob. 2.52SPCh. 2 - Each of these compounds can react as a nucleophile...Ch. 2 - Prob. 2.54SPCh. 2 - Give a definition and an example for each class of...Ch. 2 - Circle the functional groups in the following...Ch. 2 - Prob. 2.57SP
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- Sketch two graphs: (a) percent dissociation for weak acid HA versus the initial concentration of HA ([HA]0) and(b) H+ concentration versus [HA]0. Explain both.arrow_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_forwardSalicylic acid, HOC6H4CO2H, and its derivatives have been used as pain relievers for a long time. Salicylic acid occurs in small amounts in the leaves, bark, and roots of some vegetation (most notably historically in the bark of the willow tree). Extracts of these plants have been used as medications for centuries. The acid was first isolated in the laboratory in 1838. (a) Bath functional groups of salicylic acid ionize in water, with Ka=1.0103 for the—CO2H group and 4.201013 for the -OH group. What is the pH of a saturated solution of the acid (solubility = 1.8 g/L).. (b) Aspirin was discovered as a result of efforts to produce a derivative of salicylic acid that would not be irritating to the stomach lining. Aspirin is acetylsalicylic acid, CH3CO2C6H4CO2H. The -CO2H functional group is still present, but its acidity is reduced, Ka=3.0104. What is the pH of a solution of aspirin with the same concentration as a saturated solution of salicylic acid (See Part a). (c) Under some conditions, aspirin reacts with water and forms a solution of salicylic acid and acetic acid: CH3CO2C6H4CO2H(aq)+H2O(l)HOC6H4CO2H(aq)+CH3CO2H(aq) i. Which of the acids, salicylic acid or acetic acid, produces more hydronium ions in such a solution? ii. What are the concentrations of molecules and ions in a solution produced by the hydrolysis of 0.50 g of aspirin dissolved in enough water to give 75 mL of solution?arrow_forward
- Use Table 13-3 to help answer the following questions. a. Which is the stronger base, ClO4 or C6H5NH2? b. Which is the stronger base, H2O or C6H5NH2? c. Which is the stronger base, OH or C6H5NH2? d. Which is the stronger base, C6H5NH2 or CH3NH2?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_forward
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