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. CH,ČCH, H CH,CH, H Acetone Ethane pK, 20.2 pK, 51

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. CH,ČCH, H CH,CH, H Acetone Ethane pK, 20.2 pK, 51

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 4.48AP: As we shall see in Chapter 19, hydrogens on a carbon adjacent to a carbonyl group are far more...

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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.
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+
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.
For each equation, label the Lewis acid and the Lewis base. In addition, show all unshared pairs of electrons on the reacting atoms and use curved arrows to show the flow of electrons in each reaction. (a) F + BF3 BF4
Which compound of each of the following pairs is the stronger acid/base? H3AsO3 or H3AsO4 H2SO4 or H2SO3 P3- or S3- SiO32- or SO32- NO2- or NO3-
Which one of the following is NOT basic? OH- HPO4^2- NO3- SO4^2- ClO4- In the following reaction in aqueous solution, the acid reactant is __________, and its conjugate base product is __________. CH3NH2 + HSO4^- <–> CH3NH3^+ + SO4^2– CH3NH2; CH3NH3+ HSO4-; SO4^2- CH3NH2; SO4^2- HSO4-; H3O+ HSO4-; CH3NH3+ Three acids found in foods are lactic acid (in milk products), oxalic acid (in rhubarb), and malic acid (in apples). The pKa values are LA = 3.88, OA = 1.23, and MA = 3.40. Which list has the conjugate bases of these acids in order of decreasing strength? * Lactate > oxalate > malate Oxalate > Lactate > malate Oxalate > malate > lactate malate > lactate > Oxalate Lactate > malate > oxalate
Acetonitrile (CH3CN) has a pKa of 25, making it more acidic than many other compounds having only C – H bonds. Draw Lewis structures for acetonitrile and its conjugate base. Use resonance structures to account for the acidity of acetonitrile.
Find the pKa of the acids (or conjugate acids of the given base) below. Then, draw the form that is predominant at pH = 3, 7, 12 for each of the compounds:
How did you know the molecules were weak or strong acid? Please give the pKa if that's the method you used. Please explain in detail.
On what account is H2SO4 considered a stronger acid then H2SO3?
What is the conjugate acid of HAsO4-2? H3O+ H2AsO4- H3AsO4 H3As AsO4-3
Why is HCl so acidic? For example, why is H-Cl more acidic than H-S-CH3? Isn't the conjugate base's negative charge more stabilized with a sulfur and extra methyl group (by the induction effect)? While Cl is more electronegative than Sulfur, I would assume Cl being alone as its own ion would make it less stable.