When ethanol (pKa 15.9) is mixed with sodium metal, sodium ethoxide is formed. 2 CH,CH,OH + 2 Na > 2 CH,CH,0- Nat + H2 ethanol sodium ethoxide (a) Which among the compounds below will favorably react with sodium ethoxide through an acid/base reaction? Explain your choice. CH3CO,H (pKa 4.8) Н-СЕС-Н (рКа 25) H20 (pKa 14.0) NH: (pKa 38) (b) Draw a rational mechanism for the favored acid/base reaction in (a). Choose only one of th possible reactions in case there is more than one answer in the above item.

When ethanol (pKa 15.9) is mixed with sodium metal, sodium ethoxide is formed. 2 CH,CH,OH + 2 Na > 2 CH,CH,0- Nat + H2 ethanol sodium ethoxide (a) Which among the compounds below will favorably react with sodium ethoxide through an acid/base reaction? Explain your choice. CH3CO,H (pKa 4.8) Н-СЕС-Н (рКа 25) H20 (pKa 14.0) NH: (pKa 38) (b) Draw a rational mechanism for the favored acid/base reaction in (a). Choose only one of th possible reactions in case there is more than one answer in the above item.

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

Chapter18: Functional Derivatives Of Carboxylic Acids

Section: Chapter Questions

Problem 18.59P

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