Rank the following organic molecules in order of decreasing acidity. That is, select '1' in the second column for the most acidic molecule, '2' for the next most acidic molecule, and so on. HO CI ○ CI CI CI སྤུ CI CI OH (Choose one) (Choose one) O (Choose one) OH (Choose one) HO CI CI Explanation Check X

Rank the following organic molecules in order of decreasing acidity. That is, select '1' in the second column for the most acidic molecule, '2' for the next most acidic molecule, and so on. HO CI ○ CI CI CI སྤུ CI CI OH (Choose one) (Choose one) O (Choose one) OH (Choose one) HO CI CI Explanation Check X

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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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)
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.
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?
Use Table 13-2 to order the following from the strongest to the weakest acid. HClO2,H2O,NH4+,HClO4
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+
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)
A very strong base can remove a proton from methylamine:
(E) Label each of the following as strong acid, strong base, or neither.
Gastric juice, the digestive ?uid produced in the stomach, contains hydrochloric acid, HCl, Milk of Magnesia, a suspension of solid Mg(OH)2 in an aqueous medium, is sometimes used to neutralize-excess stomach acid. Write a complete balanced equation for the neutralization reaction, and identify the conjugate acid—base pairs.
Consider the following four solutions: (1) apple juice, pH 3.8, (2) pickle juice, pH 3.5, (3) carbonated beverage, pH 3.0, and (4) drinking water, pH 7.2. a. Which solution has the highest [H3O+]? b. Which solution has the highest [OH]? c. List the solutions in order of increasing acidity. d. List the solutions in order of decreasing basicity.
Salicylic acid, HOC6H4CO2H, and its derivatives have been used as pain relievers for a long time. Salicylic acid occurs in small amounts in the leaves, bark, and roots of some vegetation (most notably historically in the bark of the willow tree). Extracts of these plants have been used as medications for centuries. The acid was first isolated in the laboratory in 1838. (a) Bath functional groups of salicylic acid ionize in water, with Ka=1.0103 for the—CO2H group and 4.201013 for the -OH group. What is the pH of a saturated solution of the acid (solubility = 1.8 g/L).. (b) Aspirin was discovered as a result of efforts to produce a derivative of salicylic acid that would not be irritating to the stomach lining. Aspirin is acetylsalicylic acid, CH3CO2C6H4CO2H. The -CO2H functional group is still present, but its acidity is reduced, Ka=3.0104. What is the pH of a solution of aspirin with the same concentration as a saturated solution of salicylic acid (See Part a). (c) Under some conditions, aspirin reacts with water and forms a solution of salicylic acid and acetic acid: CH3CO2C6H4CO2H(aq)+H2O(l)HOC6H4CO2H(aq)+CH3CO2H(aq) i. Which of the acids, salicylic acid or acetic acid, produces more hydronium ions in such a solution? ii. What are the concentrations of molecules and ions in a solution produced by the hydrolysis of 0.50 g of aspirin dissolved in enough water to give 75 mL of solution?
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.