Consider the following five species dissolved separately in liquid water at 25 °C
CHEMISTRY · Multi-part · A Level · Chemistry · Carboxylic acids and derivatives · Carboxylic acids and derivatives
Problem
Consider the following five species dissolved separately in liquid water at 25 °C.
• CH3COOH (acetic acid)
• CCl3COOH (trichloroacetic acid)
• HCOOH (formic acid)
• C6H5OH (phenol)
• NH3 (ammonia)
Answer the questions that follow.
(a) Rank the five species in order of increasing acidity (1 = weakest acid, 5 = strongest acid).
(b) Provide a detailed justification for your ranking. In your explanation, discuss how resonance delocalization, inductive effects, and the identity of the conjugate base contribute to the observed acid strengths.
(c) Based on your ranking, place the conjugate bases of the five species in order of increasing stability and explain how your ordering is consistent with the acid strengths in part (a).