Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 10.SE, Problem 46AP
Interpretation Introduction
Interpretation:
Concept introduction:
Carboxylic acids are more acidic since their conjugate bases obtained by the loss of a proton, carboxylate anions, are stablised by resonance. Alcohols are less acidic as there is no resonance stabilization possible in their conjugate bases, the alkoxide ions.
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Briefly, but clearly, explain why the –OH hydrogen in acetic acid (CH3CO2H) is more acidic than in ethanol (C2H5OH).
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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) .
Chapter 10 Solutions
Organic Chemistry
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Ch. 10.7 - How would you carry out the following...Ch. 10.8 - Rank both sets of compounds in order of increasing...Ch. 10.8 - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 14VCCh. 10.SE - Prob. 15VCCh. 10.SE - Prob. 16VCCh. 10.SE - Draw the electron-pushing mechanism for each...Ch. 10.SE - Draw the electron-pushing mechanism for the...Ch. 10.SE - The formation of Br2 from NBS first involves the...Ch. 10.SE - In light of the fact that tertiary alkyl halides...Ch. 10.SE - Alkyl halides can be reduced to alkanes by a...Ch. 10.SE - Name the following alkyl halides:Ch. 10.SE - Prob. 23APCh. 10.SE - Draw and name all of the monochlorination products...Ch. 10.SE - How would you prepare the following compounds,...Ch. 10.SE - Prob. 26APCh. 10.SE - A chemist requires a large amount of...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product would you expect from the reaction of...Ch. 10.SE - Rank the compounds in each of the following series...Ch. 10.SE - Which of the following compounds have the same...Ch. 10.SE - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 34APCh. 10.SE - Alkylbenzenes such as toluene (methylbenzene)...Ch. 10.SE - Prob. 36APCh. 10.SE - Prob. 37APCh. 10.SE - Prob. 38APCh. 10.SE - Prob. 39APCh. 10.SE - Prob. 40APCh. 10.SE - The syntheses shown here are unlikely to occur as...Ch. 10.SE - Why do you suppose its not possible to prepare a...Ch. 10.SE - Prob. 43APCh. 10.SE - Identify the reagents a–c in the following...Ch. 10.SE - Prob. 45APCh. 10.SE - Prob. 46APCh. 10.SE - Prob. 47APCh. 10.SE - The relative rate of radical bromination is...Ch. 10.SE - Prob. 49APCh. 10.SE - Predict the product and provide the entire...
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Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 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_forwardUse resonance forms of the conjugate bases to explain why methanesulfonic acid (CH3SO3H,pKa = -2.6) is a much stronger acid than acetic acid (CH3COOH, pKa = 4.8).arrow_forwardWould the carboxyl group make the 3rd option the most acidic? Or would the fluorines make the 5th one the most acidic?arrow_forward
- 6. (Chapter 15-Q37) Indole is an aromatic heterocyclic that has a benzene ring fused to a pyrrole ring. Answer the following questions. Indole 6(a) What is the hybridization of N in this molecule? = 6(b) How many pi electrons N contributes to the ring? = 6() Which orbitals contribute to form a sigma bond between N and H in this molecule? = 6(c) What is the electronic relationship of Indole to naphthalene? Give the answer by comparing number of rings and number of pi electrons in both compounds, write x rings, y pi electrons=|arrow_forwardThe compound WH2(C5H5)2 acts as a base, but TaH3(C5H5)2does not. Explain.arrow_forwardGiven 4-methylhexanoic acid1. How will the acid be deprotonated if the pH in the solution is adjusted so that the pH> pKa? 2. How will the acid be deprotonated if the pH in the solution is adjusted so that the pH = pKa? 3. How will the acid be deprotonated if the pH the solution is adjusted so that pH <pKa?arrow_forward
- Ketones typically have a pka of approximately 20. While this is certainly not a strong acid it is much stronger than a typical alkane sp3-CH. using acetone as an example, explain why ketones are much more acidic than Alkanes.arrow_forwardAn amine R. However, when an imine is protonated, the resulting iminium ion is highly electrophilic: R An ammonium ion An imine R. R R An iminium ion Explain this difference in reactivity between an ammonium ion and an iminium ion. O The ammonium ion is a stronger acid, making it less electrophilic. • The iminium ion has a resonance structure with an empty p orbital on the carbon atom, making it electrophilic. The pi bond in the iminium ion is electron-rich, making it more electrophilic.. O The iminium ion is resonance-stabilized, making it more reactive.arrow_forward6. Predict the position of the equilibrium and calculate the equilibrium constant, Keq, for the following acid-base reaction. CH3NH₂+ + CH3COO- CH3NH₂ + CH3COOH methylamine acetic acid acetate ion pK₂ = 4.74 methylammonium ion pK₂ = 10.64arrow_forward
- + Br₂ what is/are the products?arrow_forwardHow does resonance affect the acidity of a compound? Why is phenol more acidic in some alcohols and why is carboxylic acid more acidic?arrow_forward78) Why are primary alcohols more acidic than tertiary alcohols, in general? Because tertiary alcohols have less acidic hydrogens. Because primary alcohols have less electron-donating groups which create more effective charge separation between oxygen and hydrogen atom, making it more acidic. Because primary alcohols are more polar than tertiary alcohols. Because primary alcohols have less electron-donating groups which decrease electron density on oxygen, making it more susceptible for H+ to depart from the structure.arrow_forward
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