Incorrect Your answer is incorrect. Use the information in the pK table to rank the molecules in order of decreasing basicity. For example, select "1" in the second column for the strongest base and "2" for the next strongest base and so on. Molecules PK table Br 4-weakest base CH 48 4 CHÍNH, 10.6 HF 3.17 NH, 1-strongest base NH 38 CH,SH 10.4 H₂O+ -1.7 F 3 H₂ 36 HCN 9.4 CH,OH -2.2 H₂O 2 CHÍNH, 33 NH 9.2 H2SO4 -3.0 H₂O 15.7 H₂S 7.00 HCI -7 CH₂OH 15.5 CH,CO,H 4.76 HBr 6 ☑ G

Incorrect Your answer is incorrect. Use the information in the pK table to rank the molecules in order of decreasing basicity. For example, select "1" in the second column for the strongest base and "2" for the next strongest base and so on. Molecules PK table Br 4-weakest base CH 48 4 CHÍNH, 10.6 HF 3.17 NH, 1-strongest base NH 38 CH,SH 10.4 H₂O+ -1.7 F 3 H₂ 36 HCN 9.4 CH,OH -2.2 H₂O 2 CHÍNH, 33 NH 9.2 H2SO4 -3.0 H₂O 15.7 H₂S 7.00 HCI -7 CH₂OH 15.5 CH,CO,H 4.76 HBr 6 ☑ G

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter4: Acids And Bases

Section: Chapter Questions

Problem 4.21P: Answer true or false to the following statements about the mechanism of acid-base reactions. (a) The...

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Complete a net ionic equation for each proton-transfer reaction using curved arrows to show the flow of electron pairs in each reaction. In addition, write Lewis structures for all starting materials and products. Label the original acid and its conjugate base; label the original base and its conjugate acid. If you are uncertain about which substance in each equation is the proton donor, refer to Table 4.1 for the relative strengths of proton acids. (a) NH3+HCl (b) CH3CH2O+HCl (c) HCO3+OH (d) CH3COO+NH4+
Several acids and their respective equilibrium constants are: Which is the strongest acid? Which is the weakest acid? Which acid has the weakest conjugate base? Which acid has the strongest conjugate base?
16-27 Guanidine, p/Ca 13.6, is a very strong base, almost as basic as hydroxide ion. NH NH2+ II II H2N—C—NH2 + H2O H2N—C—NH2 + OH" Guanidine Guanidinium ion pKb = 13.6 Complete the Lewis structure for guanidine, showing all valence electrons. The remarkable basicity of guanidine is attributed to the fact that the positive charge on the guanidinium ion is delocalized by resonance over the three nitrogen atoms. This delocalization increases the stability of the guanidinium ion relative to the ammonium ion or substituted ammonium ions. Draw three equivalent contributing structures for the guanidinium ion and show by the use of curved arrows how these three contributors are related. Propose an explanation for the fact that protonation occurs on the C=NH nitrogen rather than on one of the —NH., nitrogens. (Hint: Consider the resonance stabilization of the structure formed by protonation on a —NH., nitrogen compared with the resonance stabilization of the structure formed by protonation on the =NH nitrogen.) Predict the N—C—N bond angles in the hybrid. Which is the stronger acid, the ammonium ion or the guanidinium ion?
The following are equivalent ways of asking about the acidity of an H atom: • What is the most acidic H on the molecule? • Which H is associated with the published pKa value? • Which H on the molecule is easiest to remove? • Which H on the molecule takes the least energy to remove? • Which bond to an H is most polarized? • For which H atom is removal least uphill in energy? • Which bond to an H atom, when broken, results in the lowest PE conjugate base? We will often find the last of these questions is easiest to answer. To do this, find all the different Hatoms on the molecule, and draw all possible conjugate bases.Only the lowest-energy one is the “real” conjugate base. Identify this structure, and you have found the most acidic H. Use this strategy to find the most acidic H on each of the following molecules. Note: Each structure hasat least three different kinds of H’s, so draw at least three unique conjugate bases for each.
Use Table 13-2 to order the following from the strongest to the weakest acid. HClO2,H2O,NH4+,HClO4
A very strong base can remove a proton from methylamine:
For the previous four questions, label each molecule that appears in the question or your answer asstrong acid, strong base, weak acid, or weak base.
Complete the equation for the reaction between each Lewis acid-base pair. In each equation, label which starting material is the Lewis acid and which is the Lewis base; use curved arrows to show the flow of electrons in each reaction. In doing this problem, it is essential that you show valence electrons for all atoms participating in each reaction. (a) (b) (c) (d)
In each of the following acid-base reactions, identify the Brnsted acid and base on the left and their conjugate partners on the right. (a) C2H5N(aq) + CH3CO2H(aq) C5H5NH+(aq) + CH3CO2(aq) (b) N2H4(aq) + HSO4(aq) N2H5+(aq) + SO42(aq) (c) [Al(H2O)6]3+ (aq) + OH(aq) [Al(H2O)5OH]2+ (aq) + H2O+()
Place the species in each of the following groups in order of increasing acid strength. a. H2O, H2S, H2Se (bond energies: HO, 467 kJ/mol; HS, 363 kJ/mol; HSe, 276 kJ/mol) b. CH3CO2H, FCH2CO2H, F2CHCO2H, F3CCO2H c. NH4+, HONH3+ d. NH4+, PH4+ (bond energies: NH, 391 kJ/mol; PH, 322 kJ/mol) Give reasons for the orders you chose.
Which has the larger numerical value? (a) The pKa of a strong acid or the pKa of a weak acid (b) The Ka of a strong acid or the Ka of a weak acid
You may need Table 13-2 to answer the following questions. a. Which is the stronger base, Cl or H2O? b. Which is the stronger base, H2O or NO2? c. Which is the stronger base, CNor OC6H5?