Cyclohexane-1,3-dione is a diketone that can act as a Brønsted-Lowry acid despite not having a hydrogen bonded to an electronegative atom. In this molecule, a hydrogen bonded to carbon 2 is acidic. Hexanol is an alcohol and hence can also act as a Brønsted-Lowry acid. a) Draw the stabilized conjugate bases of cyclohexane-1,3-dione and hexanol. No need to draw the protonated forms. b) Based on your illustration in part (a), predict which one has a lower pKa between cyclohexane-1,3-dione and hexanol. Explain why.

Cyclohexane-1,3-dione is a diketone that can act as a Brønsted-Lowry acid despite not having a hydrogen bonded to an electronegative atom. In this molecule, a hydrogen bonded to carbon 2 is acidic. Hexanol is an alcohol and hence can also act as a Brønsted-Lowry acid. a) Draw the stabilized conjugate bases of cyclohexane-1,3-dione and hexanol. No need to draw the protonated forms. b) Based on your illustration in part (a), predict which one has a lower pKa between cyclohexane-1,3-dione and hexanol. Explain why.

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

Chapter10: Alcohols

Section10.7: The Pinacol Rearrangement

Problem FQ

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