Trifluoroethanol (CF3CH2OH, pKa = 12.5) is more acidic than ethanol (CH3CH2OH, pKa = 16). Provide a three-dimensional structure for each conjugate base and draw the orbitals for all lone pairs. Provide a succinct explanation for the greater acidity of trifluoroethanol.

Trifluoroethanol (CF3CH2OH, pKa = 12.5) is more acidic than ethanol (CH3CH2OH, pKa = 16). Provide a three-dimensional structure for each conjugate base and draw the orbitals for all lone pairs. Provide a succinct explanation for the greater acidity of trifluoroethanol.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter27: Amines

Section: Chapter Questions

Problem 7E

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Concept explainers

Diol

In chemistry there are so many chemical compounds that have a hydroxyl group but a chemical compound having two hydroxyl groups (-OH) is termed as a diol. It also implies the presence of two alcohols whereas polyols contain two or more than two hydroxyl groups (-OH). Glycol or 1,2-diol is an aliphatic diol that has two alcohol groups on adjacent carbon atoms. In industries, the most commonly used diol is ethylene glycol.

Question

Trifluoroethanol (CF3CH2OH, pKa = 12.5) is more acidic than ethanol (CH3CH2OH, pKa = 16). Provide a
three-dimensional structure for each conjugate base and draw the orbitals for all lone pairs. Provide a
succinct explanation for the greater acidity of trifluoroethanol.

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