When water is the solvent, the pKa of acetic acid (CH3CO2H) is 4.75, but when DMSO is the solvent, the pKa is 12.6.Explain why. Hint: Review Section 2.9 and consider the ability of each solvent to solvate cations and anions.

When water is the solvent, the pKa of acetic acid (CH3CO2H) is 4.75, but when DMSO is the solvent, the pKa is 12.6.Explain why. Hint: Review Section 2.9 and consider the ability of each solvent to solvate cations and anions.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter13: Substitution

Section: Chapter Questions

Problem 29CTQ

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Concept explainers

Amines

Amines are organic compounds with a nitrogen atom having a lone pair of electrons on it. They are derived from ammonia (NH3) wherein hydrogen atoms are substituted by an aryl or alkyl group.

Question

When water is the solvent, the pK_a of acetic acid (CH₃CO₂H) is 4.75, but when DMSO is the solvent, the pK_ais 12.6.Explain why.

Hint: Review Section 2.9 and consider the ability of each solvent to solvate cations and anions.

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