Conjugate base acid 1a. Consider the reaction AH(+) + H₂O →> A:(-) + H3O+). For the following named acids: a) draw the structure of the acid, b) give the approximate pKa of the conjugate acid in units of 5, c) give the name of the conjugate base, and d) draw the structure of the conjugate base. Dimethyl sulfoxide pKa Acrylic Acid pKa Ethyl Acetate pKa Benzamide pKa

Conjugate base acid 1a. Consider the reaction AH(+) + H₂O →> A:(-) + H3O+). For the following named acids: a) draw the structure of the acid, b) give the approximate pKa of the conjugate acid in units of 5, c) give the name of the conjugate base, and d) draw the structure of the conjugate base. Dimethyl sulfoxide pKa Acrylic Acid pKa Ethyl Acetate pKa Benzamide pKa

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 4.10P: Complete a net ionic equation for each proton-transfer reaction using curved arrows to show the flow...

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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+
Define or illustrate the meaning of the following terms: a. Ka reaction b. Ka equilibrium constant c. Kb reaction d. Kb equilibrium constant e. conjugate acidbase pair
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 reactions illustrate Brnsted acid-base behavior. Complete each equation. a.HI(aq)+?H3O+(aq)+I(aq) b.NH3(l)+?NH4++NH2 c.H2C2O4(aq)+H2O(l)?+HC2O4(aq) d.H2N2O2(aq)+H2O(l)H3O+(aq)+? e.?+H2O(l)H3O+(aq)+CO32(aq)
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?
Answer true or false to the following statements about the mechanism of acid-base reactions. (a) The acid and base must encounter each other by a collision in order for the proton to transfer. (b) All collisions between acids and bases result in proton transfer. (c) During an acid-base reaction the lone pair on the base fills the A-H antibonding sigma orbital.
Find the value of Kb for the conjugate base of the following organic acids. (a) picric acid used in the manufacture of explosives; Ka = 0.16 (b) trichloroacetic acid used in the treatment of warts; Ka = 0.20
Acid-Base Equilibria Many factors contribute to the acidity of organic compounds. Electronegativity, resonance, induction, hybridization, aromaticity, and atomic size, all play a role. In the following comparisons, you are asked to identify the factor(s) that would be most important to analyze when predicting relative acidity, and then to predict the trend in acidity and pKa values. For each of the following pairs of compounds answer the following two multiple-choice questions. 1. What factor(s) are the most important to consider when predicting the relative acidity of the two compounds? a. Electronegativity of the atom possessing the hydrogen. b. Resonance stabilization of the anionic conjugate base. c. Inductive stabilization of the anionic conjugate base. d. Hybridization of the atom possessing the hydrogen. e. The atomic size of the atom possessing the hydrogen.
How do the components of a conjugate acid—base pair differ from one another4? Give an example of a conjugate acid—base pair to illustrate your answer.
Which of the following compounds or ions has the weakest conjugate base? Briefly explain your choice. a) HCN b) HClO c) NH4+
A very strong base can remove a proton from methylamine:
Using the diagrams shown in Problem 10-37, which of the four acids is the weakest acid?