5) Rank the following sets of compounds in order of decreasing acidity (most acidic to least acidic), and choose the justification(s) for each ranking. (a) OH V SH я вон CH most acidic (lowst pKa) least acidic (highest pKa) Effect(s) Effect(s) Effect(s) inductive effect O inductive effect O inductive effect electronegativity electronegativity O electronegativity resonance polarizability resonance polarizability O resonance O polarizability hybridization Ohybridization O hybridization о € SH B SH 'SH V SH most acidic (lowst pKa) least acidic (highest pKa) Effect(s) inductive effect electronegativity resonance polarizability O hybridization Effect(s) O inductive effect electronegativity resonance O polarizability hybridization 0000 Effect(s) inductive effect electronegativity resonance O polarizability Ohybridization (c) H CH3 H CH3 H-CH3 least acidic (highest pKa) most acidic (lowst pKa) Effect(s) inductive effect Effect(s) inductive effect Effect(s) O inductive effect electronegativity O electronegativity O electronegativity resonance resonance resonance polarizability polarizability O polarizability hybridization O hybridization O hybridization

5) Rank the following sets of compounds in order of decreasing acidity (most acidic to least acidic), and choose the justification(s) for each ranking. (a) OH V SH я вон CH most acidic (lowst pKa) least acidic (highest pKa) Effect(s) Effect(s) Effect(s) inductive effect O inductive effect O inductive effect electronegativity electronegativity O electronegativity resonance polarizability resonance polarizability O resonance O polarizability hybridization Ohybridization O hybridization о € SH B SH 'SH V SH most acidic (lowst pKa) least acidic (highest pKa) Effect(s) inductive effect electronegativity resonance polarizability O hybridization Effect(s) O inductive effect electronegativity resonance O polarizability hybridization 0000 Effect(s) inductive effect electronegativity resonance O polarizability Ohybridization (c) H CH3 H CH3 H-CH3 least acidic (highest pKa) most acidic (lowst pKa) Effect(s) inductive effect Effect(s) inductive effect Effect(s) O inductive effect electronegativity O electronegativity O electronegativity resonance resonance resonance polarizability polarizability O polarizability hybridization O hybridization O hybridization

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 4.33P: Complete the equation for the reaction between each Lewis acid-base pair. In each equation, label...

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Similar questions

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)
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.
A very strong base can remove a proton from methylamine:
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.
(E) Label each of the following as strong acid, strong base, or neither.
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?
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.
For each molecule below, draw the conjugate acid or conjugate base or both if the molecule hasboth a conjugate acid and a conjugate base (e.g., water).
Rank the following compounds in order of increasing acidity, and explain your ranking. Br E A A COOH O₂N B COOH (least acidic) < с (most acidic) COOH The strongest acid has a strong electron-withdrawing group base. The weakest acid has a strong electron-donating group H₂C that will D B COOH destabilize that will stabilize the E .COOH Dositive D charge in its conjugate the negative charge in its A
Rank the acids in the table below from strongest (1)to weakest (4). The most acidic H atom in each acid has been highlighted.