Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Textbook Question
Chapter 3, Problem 5PP
PRACTICE PROBLEM 3.5
Formic acid
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Identify the Lewis acid and Lewis base in each equation:
Consider two acids: HCO2H (formic acid, pKa = 3.8) and pivalic acid [(CH3)3CCO,H, pK = 5.0].
(a) Which acid has the larger K? (b) Which acid is the stronger acid? (c) Which acid forms the
stronger conjugate base? (d) When each acid is dissolved in water, for which acid does the
equilibrium lie further to the right?
%3D
The pKa values in Table 2.1 span a large range (-7 to 50). The pK, scale is logarithmic.
small difference in pK, translates into a large numerical difference, For example, the diffe
between the pK, of NH3 (38) and CH2=CH, (44) is six pKa units. This means that NH, is
one million times more acidic than CH,=CH,.
Which, if any, of the following statements are true? (a) The stronger the base, the smaller the pKb. (b) The stronger the base, the larger the pKb. (c) The stronger the base, the smaller the Kb. (d) The stronger the base, the larger the Kb. (e) The stronger the base, the smaller the pKa of its conjugate acid. (f) The stronger the base, the larger the pKa of its conjugate acid.
Chapter 3 Solutions
Organic Chemistry
Ch. 3 - Prob. 1PPCh. 3 - PRACTICE PROBLEM 3.2
Write equations showing the...Ch. 3 - PRACTICE PROBLEM 3.3 Which of the following are...Ch. 3 - Prob. 4PPCh. 3 - PRACTICE PROBLEM 3.5 Formic acid (HCO2H) has...Ch. 3 - Prob. 6PPCh. 3 - Prob. 7PPCh. 3 - Prob. 8PPCh. 3 - PRACTICE PROBLEM 3.9 Predict the outcome of the...Ch. 3 - Prob. 10PP
Ch. 3 - Prob. 11PPCh. 3 - Prob. 12PPCh. 3 - Prob. 13PPCh. 3 - Prob. 14PPCh. 3 - Prob. 15PPCh. 3 - Prob. 16PPCh. 3 - Prob. 17PPCh. 3 - What is the conjugate base of each of the...Ch. 3 - List the bases you gave as answers to Problem 3.20...Ch. 3 - 3.22 What is the conjugate acid of each of the...Ch. 3 - List the acids you gave as answers to Problem 3.22...Ch. 3 - Designate the Lewis acid and Lewis base in each of...Ch. 3 - Prob. 23PCh. 3 - Prob. 24PCh. 3 - Write an equation, using the curved-arrow...Ch. 3 - When methyl alcohol is treated with NaH, the...Ch. 3 - 3.30 What reaction will take place if ethyl...Ch. 3 - 3.31 (a) The of formic acid. What is the? (b)...Ch. 3 - Acid HA has pKa=20; acid HB has pKa=10. (a) Which...Ch. 3 - Prob. 30PCh. 3 - 3.34 (a) Arrange the following compounds in order...Ch. 3 - 3.35 Arrange the following compounds in order of...Ch. 3 - 3.36 Arrange the following in order of increasing...Ch. 3 - Prob. 34PCh. 3 - 3.38 Supply the curved arrows necessary for the...Ch. 3 - Glycine is an amino acid that can be obtained from...Ch. 3 - 3.40 Malonic acid, , is a diprotic acid. The for...Ch. 3 - 3.41 The free-energy change, , for the ionization...Ch. 3 - 3.42 At the enthalpy change, , for the ionization...Ch. 3 - The compound at right has (for obvious reasons)...Ch. 3 - 3.44.
(a) Given the above sequence of...Ch. 3 - Prob. 42PCh. 3 - Prob. 43PCh. 3 - 3.47 As noted in Table 3.1, the of acetone, , is...Ch. 3 - Formamide (HCONH2) has a pKa of approximately 25....Ch. 3 - List all the chemical species likely to be present...Ch. 3 - Prob. 2LGPCh. 3 - Prob. 3LGPCh. 3 - Prob. 4LGPCh. 3 - Prob. 1QCh. 3 - Which of the following is the strongest base? (a)...Ch. 3 - Prob. 3QCh. 3 - Prob. 4QCh. 3 - Prob. 5QCh. 3 - Which would be the weakest base? (a) CH3CO2Na (b)...Ch. 3 - What acid-base reaction (if any) would occur when...Ch. 3 - The pKa of CH3NH3+ equals 10.6; the pKa of...Ch. 3 - 3.9 Supply the missing reagents.
Ch. 3 - 3.10 Supply the missing intermediates and...
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- Consider two acids: HCO,H (formic acid, pKa = 3.8) and pivalic acid [(CH3)3CCO2H, pKa = 5.0]. (a) Which acid has the larger K,? (b) Which acid is the stronger acid? (c) Which acid forms the stronger conjugate base? (d) When each acid is dissolved in water, for which acid does the equilibrium lie further to the right?arrow_forwardGive correct handwritten answerarrow_forward(a) Papaverine hydrochloride is an alkaloid drug used as a muscle relaxant, particularly for acute myocardial infarctions and angina It is a weak acid. If a 0.205 M solution of papaverine hydrochloride has a pH of 3.31, what is its Ka?arrow_forward
- (a) Given that Ka for acetic acid is 1.8 x 10-5 and that hypochlorous acid is 3.0 x10-8 , which is a stronger acid? (b) Which is the stronger base, the acetate ion or the hypochlorite ion? (c) calculate the Kb values for the CHCOO- and ClO- .arrow_forwardLike any equilibrium constant, Kw changes with temperature. (a) Given that autoionization is endothermic, how does Kw change with rising T ? Explain with a reaction that includes heat as reactant or product. (b) In many medical applications, the value of Kw at 37°C (body temperature) may be more appropriate than the value at 25°C, 1.0 x 10-14. The pH of pure water at 37°C is 6.80. Calculate Kw, pOH, and [OH-] at this temperature.arrow_forwardA solution is made by dissolving 44.1 g of Ba(NO₂)₂ in 500.0 mL of water. (a) Does Ba²⁺ have any acidic or basic properties? (b) Does NO₂⁻ have any acidic or basic properties? (c) As NO₂⁻ is a base, write the basic equilibrium equation that exists in solution (d) What is the value of Kb for NO₂⁻? The Ka of HNO₂ is 4.5 × 10⁻⁴. (e) Determine the pH of the solutionarrow_forward
- Succinic acid (H2C4H6O4), which we will denote H2Suc,is a biologically relevant diprotic acid with the structureshown below. At 25 °C, the acid-dissociation constants forsuccinic acid are Ka1 = 6.9 x 10-5 and Ka2 = 2.5 x 10-6.(a) Determine the pH of a 0.32 M solution of H2Suc at25 °C, assuming that only the first dissociation is relevant.(b) Determine the molar concentration of Suc2 - in thesolution in part (a). (c) Is the assumption you made in part(a) justified by the result from part (b)? (d) Will a solutionof the salt NaHSuc be acidic, neutral, or basic?arrow_forward3. The pH of a 0.10 M solution of hydrazine, H₂NNH2, is 10.54. (a) Is hydrazine a weak base or acid? How do you know from the chemical formula? How do you know from the pH? (b) What is the concentration of OH ions, [OH-], in this solution? (c) Calculate the value of K, for hydrazine. Additional Problem: Beaker A, containing 200 mL of 0.150 M HI, and Beaker B, containing 200 mL of 0.100 M Ca(OH)2, are poured into a new Beaker C. (a) Calculate the initial pH values of the solutions in Beakers A and B. (b) Write out the acid-base neutralization reaction that occurs once the contents of Beakers A and B are mixed. Is one reactant in excess? (c) Determine the pH of the resulting solution in Beaker C.arrow_forward3c.) Suppose it is desired to maintain the pH of a solution at 4.2 using only acetic acid and sodium acetate. Would the concentration of acetic acid or sodium acetate have to be higher in the solution? O sodium acetate O acetic acidarrow_forward
- 2. Barbituric acid, HC,H,N,O, a weak organic acid used to manufacture hypnotic drugs and some plastic, has a Ka of 9.8 x 10 An industrial process requires a 0.25 mol/L solution of Barbituric acid. (a) Calculate the H° and pH of the solution. (b) What is the percent ionization of the acid?arrow_forwardFor each conjugate acid-base pair, identify the first species as an acid or a base and the second species as its conjugate acid or base. In addition, draw Lewis structures for each species, showing all valence electrons and any formal charge. (a) CH3CH2O- CH3CH2OHarrow_forward(a) Describe what happens when each of the following molecules is separately dissolved in water and illustrate with an equation in each case: ethanoic acid (CH3COOH) ammonia (NH3) (b) Identify the conjugate acids and bases in the substances mentioned in question 7(a) above. (c) Explain the difference between: (i) a strong acid and weak acid and (ii) a strong base and a weak basearrow_forward
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