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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Check out a sample textbook solutionStudents have asked these similar questions
The base methylamine (
CH3NH₂) has a
Kb of
5.0 x 10-4. A closely related base, trimethylamine (
(CH3)3N), has a
Kb of
7.4 x 10-5.
a Which of the two bases is stronger?
methylamine
trimethylamine
Correct
Since methylamine has the larger K₁, methylamine is the stronger base.
b Calculate the pH of a 0.38 M solution of the stronger base.
pH =
Using 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.
The acid-catalyzed hydrolysis of an ester converts an
ester into a carboxylic acid. Although there are two O
atoms that can be protonated, the first step in the
mechanism is believed to be protonation of the oxygen
in the C=0 group. Based on charge stability, why is it
favorable to protonate that oxygen? Hint: Draw out the
products of each protonation.
+ Hо
HO,
НО
Carboxylic
acid
Ester
Alcohol
Chapter 10 Solutions
Organic Chemistry
Ch. 10.1 - Prob. 1PCh. 10.1 - Draw structures corresponding to the following...Ch. 10.2 - Prob. 3PCh. 10.2 - Taking the relative reactivities of 1°, 2°, and...Ch. 10.4 - Prob. 5PCh. 10.4 - The major product of the reaction of...Ch. 10.4 - Prob. 7PCh. 10.5 - Prob. 8PCh. 10.6 - Prob. 9PCh. 10.6 - How might you replace a halogen substituent by a...
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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- K Calculate the pH of a 0.295 M solution of ethylenediamine (H₂NCH₂CH₂NH₂). The pKa values for the acidic form of ethylenediamine (HFNCH₂CH₂NH3) are 6.848 (pKat) and 9.928 (pK₁2). pH = Calculate the concentration of each form of ethylenediamine in this solution at equilibrium. [H₂NCH₂CH₂NH₂] = [H₂NCH₂CH₂NH] = [HNCH₂CH₂NH3] = M M Marrow_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. (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_forward
- 2. Will a 0.10 molar solution of CH3NH3OCN (methylamine cyanate) produce a basic or acidic solution. Explain quantitatively.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_forwardWhich of the following compounds is most basic? OH | OH = || ||| NH₂ NH₂ IVarrow_forward
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