Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 3, Problem 48P
Formamide
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Phenylamine is an aromatic amine that is used in the manufacture of dyes. When absorbed through the skin itcauses the Fe+2 in hemoglobin to become oxidized into Fe+3, resulting in the formation of methemoglobin whichcannot bind to or transport oxygen. Phenylamine is soluble in water and acts as a weak base.C6H5NH2 (aq) + H2O (ℓ) ⇋ C6H5NH3+ (aq) + OH- (aq)a. When you measure the concentrations of the ionized substances you find them to be:[C6H5NH2] = 0.234 mol/L [C6H5NH3+] = 2.8 x 10-5 mol/L [OH-]= 2.8 x 10-5 mol/LIf the Kb is 4.27 x 10-10, is the reaction at equilibrium? If not, which direction does it need to move (rightor left) to reach equilibrium? Explain.
b. At equilibrium the concentrations of the ionized substances are:[C6H5NH2] = 0.0537 mol/L [C6H5NH3+] = 4.79 x 10-6 mol/L [OH-]= 4.79 x 10-6 mol/LIf this reaction is taking place in a 2.0L container, and 1.5 moles of phenylamine were added to thereaction, what will the new concentrations of the three ionic species be when…
Propose you are given a mixture of naphthalene, propanoic acid, and diethyl amine. Explain, using a flow chart similar to that in #1, how you would separate these three compounds. Include all solvents and reagents, show the exact compound that is present at each juncture, and be clear about the experimental technique employed in each step.
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Using molecular structures, what will happen in the following situation:
* Ethyl 4-aminobenzoate is dissolved in dichloromethane and then 1 M HCl (aq) is added
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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- a) If the pH value of an aqueous solution of trimethylamine [(CH3)3N] is 10.75, what should be the molarity of this solution? (CH3)3N + H2O ↔ (CH3)3NH+ + OH-, Kb = 6,3 × 10-5 b) What will be the pH of the solution prepared by dissolving 8.35 g of aniline hydrochloride (C6H5NH3+Cl-) in 750 mL of 0.215 M aniline (C6H5NH2)? Is this solution an effective buffer? Explain (Kb = 7,4 × 10-10 for aniline, C: 12.0 g / mol, H: 1.0 g / mol, N: 14.0 g / mol, Cl: 35.4 g / mol) .arrow_forwardpropanoic acid + methanol (in concentrated sulfuric acid)arrow_forwardSuggest a possible structure for Compound X.arrow_forward
- a) If the pH value of an aqueous solution of trimethylamine [(CH3) 3N] is 10.75, what should be the molarity of this solution? (CH3) 3N + H2O ↔ (CH3) 3NH + + OH-, Kb = 6.3 × 10-5 b) What will be the pH of the solution prepared by dissolving 8.35 g of aniline hydrochloride (C6H5NH3 + Cl-) in 750 mL of 0.215 M aniline (C6H5NH2)? Is this solution an effective buffer? Explain (Kb = 7.4 × 10-10 for aniline, C: 12.0 g / mol, H: 1.0 g / mol, N: 14.0 g / mol, Cl: 35.4 g / mol) .arrow_forwardPlace the binders below in descending order of acidity (pi) and justify your choice: CH3CN; (C2H5)2O; PCl3; As(C6H5)3; (C2H5)3Narrow_forwardUsing your knowledge on structural effects, account for the following observations by giving appropriate explanations. 1) Boron trifluoride (BF3) is a stronger Lewis acid than trimethyl borate [(CH3O)3B]. 2) Piperidine is a much stronger Lewis base than pyridine.arrow_forward
- 1. Write the equilibrium-constant expressions and obtain numerical values for each constant in(a) the basic dissociation of aniline, C6H5NH2 .(b) the acidic dissociation of hypochlorous acid, HClO.(c) the acidic dissociation of methyl ammonium hydrochloride, CH3NH3Cl.(d) the basic dissociation of NaNO2 .(e) the dissociation of H3AsO3 to H3O + and AsO33- 2. The chemicals A and B react as follows to produce C and D: A + B ↔ C + DKe = [C] [D] [A] [B] The equilibrium constant Ke has a value of 0.30. Assume 0.20 mol of A and 0.50 mol of B are dissolved in 1.00 L, and the reaction proceeds. Calculate the concentrations of reactants [A], [B] and products [C], [D] at equilibrium. Using step-by-step processarrow_forward(2) Caffeine (C8H10N4O2) is a weak base with a pKь of 10.4. Calculate the pH of a solution containing a caffeine concentration of 455 mg/L.arrow_forwardCalculate the pH of a 0.105 M solution of ethylenediamine (H,NCH,CH,NH,). The pKa values for the acidic form of ethylenediamine (H†NCH,CH,NH) are 6.848 (pKa1) and 9.928 (pK22). pH Calculate the concentration of each form of ethylenediamine in this solution at equilibrium. [H,NCH,CH,NH,] = M [H,NCH,CH,NH; 1 = M [HNCH,CH,NH] = Marrow_forward
- (a) Explain how NaBH, in CH;OH can reduce hemiacetal A to 1,4-butanediol (HOCH,CH,CH,CH,OH). (b) What product is formed when A is treated with Ph;P=CHCH,CH(CH),? (c) The drug isotretinoin is formed by reaction of X and Y. What is the structure of isotretinoin? Although isotretinoin (trade name Accutane or Roaccutane) is used for the treatment of severe acne, it is dispensed under strict controls because it also causes birth defects. PPha NaOCH,CH3 HO- isotretinoin HO A Br X Yarrow_forwardComplete the following equation for the dissociation of butyric acid in water, so as to illustrate unambiguously that butyric acid is a weak acid: CH3CH2CH2COOH(aq)+ H20(1)arrow_forwardUsing the data in Appendix C, determine which of the following bases is strong enough to deprotonate acetonitrile (CH3CN), so that equilibrium favors the products: (a) NaH; (b) Na2CO3; (c) NaOH; (d) NaNH2; (e) NaHCO3.arrow_forward
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