Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 3, Problem 5PP
PRACTICE PROBLEM 3.5
Formic acid
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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.
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?
In the following reactions, indicate the acid, base, conjugate acid, and conjugate base.
(a)HF + NH3→NH4++ F –
(b)NaHSO4+ HClO3⇌H2SO4+ NaClO3
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 - PRACTICE PROBLEM 3.15 Nitro groups have a large...Ch. 3 - PRACTICE PROBLEM 3.16
Your laboratory instructor...Ch. 3 - Prob. 17PPCh. 3 - Prob. 18PPCh. 3 - Prob. 19PPCh. 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 - Rank the following in order of increasing acidity.Ch. 3 - Without consulting tables, select the stronger...Ch. 3 - Designate the Lewis acid and Lewis base in each of...Ch. 3 - Prob. 27PCh. 3 - Prob. 28PCh. 3 - Write an equation, using the curved-arrow...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. 33PCh. 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. 37PCh. 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. 45PCh. 3 - Prob. 46PCh. 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. 4LGP
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- Like 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_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_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
- 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_forward(4) Which acid below would have a stronger conjugate base? Give the reason (a) HCN, Ka 6.2 x 10-10 Ka=2.3 x 10-⁹ (b) HBrO,arrow_forwardAnswer the following questions about acid-base equilibrium reactions. (a)Which is a stronger acid HX or HY in the reaction below? HX + Y –→X –+ HYK eq= 2.43 x 10 –3 (b)What is the difference between a strong acid and a weak acid in terms of equilibrium position? (c)If the Kaof H2CO3is 4.3 x 10 –7and the Kaof HF is 6.8 x 10 –4, then is the reaction below reactant favored or product favored?H2CO3+ F –→HCO3–+ HFarrow_forward
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