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 3PP
PRACTICE PROBLEM 3.3
Which of the following are potential Lewis acids and which are potential Lewis bases?
(c)
(d)
(e)
(f)
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For 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- CH3CH2OH
4.
A student has prepared 0.05 M solution of CH3-C=CH and has added to it 0.05 M solution of
potassium tert-butoxide (K" O-C(CH3)3).
(i) Write the equation for the acid-base reaction that might occur.
(ii) With curved arrows track the movements of electron pairs.
(iii) Assign Base, Acid, Conjugate acid for the base, Conjugate base for the acid.
(iv) Calculate the percentage of deprotonated methyl acetylene taking into account that pKa of
the conjugate acid of potassium tert-butoxide equals 18 and pKa of methyl acetylene equals 24.
(a)
(e)
Draw the conjugate base for each of the following acids:
OH
OH
(b)
(f)
H
N.
(c) NH3
(g) NH4+
(d) H3O+
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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- Which chemical group is most likely to be responsible for an organic molecule behaving as a base (see Concept 3.3)? (A) hydroxyl (B) carbonyl (C) amino (D) phosphatearrow_forward(a) Draw the Lewis structures for at least four species thathave the general formula where X and Y may be the same or different, and n mayhave a value from +1 to -2. (b) Which of the compoundsis likely to be the strongest Brønsted base?arrow_forwardSolve the following Given that pH = 13, 7.5 , 7.4 find: (a) pOH (b) H3O+ (c) OH-arrow_forward
- 2-11 2.19] A solution has an H+ concentration of 10-5 M. (a) What is the pH of this solution? (b) What is the pOH (Assume that the temperature of the solution is 25°C.) Answer: (a) 5 (b) 9 BMarrow_forwardWould CH3NH3C2H3O2 (salt) be neutral, basic, acidic or cannot be determined?arrow_forwardWhy is (CH3)3Cl considered to be a Lewis Acid?arrow_forward
- Which is the stronger base, (CH3)3N or H2 BO3− ?arrow_forwardFor the following five reactions: (i) Cl− + AlCl3 → AlCl4−(ii) (CH3)3N + HCl → (CH3)3NHCl(iii) OH− + H3O+ → 2H2O(iv) Co3+ + 6NH3 → Co(NH3)6(v) F− + SiF4 → SiF5− Identify the Lewis acids. Choose from the list below and enter the five letters in order. (e.g. ACEGI, BDFHJ, etc.) A) Cl− B) AlCl3 C) (CH3)3N D) HCl E) OH− F) H3O+ G) Co3+ H) NH3 I) F− J) SiF4arrow_forwardWhat is the conjugate base of each of the following acids.(3a): H2SO4(3b): H2F+(3c): CH3OH(3d): H3O+arrow_forward
- 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,.arrow_forward(a) Calculate [OH-] of a 4.40×10-1 M aqueous solution of triethylamine ((C2H5)3N, Kb = 4.0×10-4). (b)Calculate the pH of the above solution.arrow_forwardBenzoic acid (C6H5COOH) and aniline (C6H5NH2) areboth derivatives of benzene. Benzoic acid is an acid withKa = 6.3 x10-5 and aniline is a base with Ka = 4.3 x10-10. (a) What are the conjugate base of benzoic acid andthe conjugate acid of aniline? (b) Anilinium chloride(C6H5NH3Cl) is a strong electrolyte that dissociates intoanilinium ions (C6H5NH3+) and chloride ions. Which willbe more acidic, a 0.10 M solution of benzoic acid or a 0.10M solution of anilinium chloride? (c) What is the value ofthe equilibrium constant for the following equilibrium?C6H5COOH(aq) + C6H5NH2(aq) ⇌ C6H5COO-(aq) + C6H5NH3+(aq)arrow_forward
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