Give a curved arrow-pushing mechanism for the following two reactions • SHOW WHERE EVERY PROTON COMES FROM AND GOES TO • Indicate the Lewis acid and base (LA or LB) at each INTERMOLECULAR step and whether they are also Brønsted acids and bases (LA/BA or BA/BB) To preview the image click here :0: NH₂ H3O+ Heat :0: H + H-N-H H

Give a curved arrow-pushing mechanism for the following two reactions • SHOW WHERE EVERY PROTON COMES FROM AND GOES TO • Indicate the Lewis acid and base (LA or LB) at each INTERMOLECULAR step and whether they are also Brønsted acids and bases (LA/BA or BA/BB) To preview the image click here :0: NH₂ H3O+ Heat :0: H + H-N-H H

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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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.
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)
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.
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+
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
(E) Label each of the following as strong acid, strong base, or neither.
A very strong base can remove a proton from methylamine:
Each box represents an acid solution at equilibrium. Squares represent H+ ions, and circles represent the anion. Water molecules are not shown. Which figure represents a strong acid? Which figure is a weak acid?
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.