A chemist wants to perform a reaction using the reagent below, which can act as a Brønsted-Lowry base. Considering only the reagent's capacity to act as a base, check the boxes of any compounds in the table that the chemist should not use as the solvent for the reaction. Use the ALEKS Data resource to look up useful data. If all of the solvents below are acceptable, please check the box that says "All solvents are acceptable."

A chemist wants to perform a reaction using the reagent below, which can act as a Brønsted-Lowry base. Considering only the reagent's capacity to act as a base, check the boxes of any compounds in the table that the chemist should not use as the solvent for the reaction. Use the ALEKS Data resource to look up useful data. If all of the solvents below are acceptable, please check the box that says "All solvents are acceptable."

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 4.35AP: The sec-butyl cation can react as both a Brnsted-Lowry acid (a proton donor) and a Lewis acid (an...

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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.
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.
Summarize the relationship between pKa and base strength by completing the followingsentences: a. For a given base, the higher the pKa of its conjugate acid, the stronger or weaker the base. b. For a given base, the lower the pKa of its conjugate acid, the stronger or weaker the 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?
List the following bases in order of their decreasing strength strongest base first: CN,H2O,HSO3,ClO,Cl.
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.
As we shall see in Chapter 19, hydrogens on a carbon adjacent to a carbonyl group are far more acidic than those not adjacent to a carbonyl group. The anion derived from acetone, for example, is more stable than is the anion derived from ethane. Account for the greater stability of the anion from acetone.
The sec-butyl cation can react as both a Brnsted-Lowry acid (a proton donor) and a Lewis acid (an electron pair acceptor) in the presence of a watersulfuric acid mixture. In each case, however, the product is different. The two reactions are as follows: (a) In which reaction(s) does this cation react as a Lewis acid? In which reaction(s) does it react as a Brnsted-Lowry acid? (b) Write Lewis structures for reactants and products and show by the use of curved arrows how each reaction occurs.
In terms of orbitals and electron arrangements, what must be present for a molecule or an ion to act as a Lewis acid? What must be present for a molecule or an ion to act as a Lewis base?
For oxyacids, how does acid strength depend on a. the strength of the bond to the acidic hydrogen atom? b. the electronegativity of the element bonded to the oxygen atom that bears the acidic hydrogen? c. the number of oxygen atoms? How does the strength of a conjugate base depend on these factors? What type of solution forms when a nonmetal oxide dissolves in water? Give an example of such an oxide. What type of solution forms when a metal oxide dissolves in water? Give an example of such an oxide.
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+