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Chapter 46: Problem 9

Predict which is most likely to be the stronger acid: \(\mathrm{CH}_{3} \mathrm{COOH}\) or \(\mathrm{CCl}_{3} \mathrm{COOH}\). Explain your reasoning.

Short Answer

Expert verified
CCl3COOH (trichloroacetic acid) is likely to be a stronger acid than CH3COOH (acetic acid), because the presence of electron-withdrawing chlorine atoms makes its conjugate base more stable.

Step by step solution

01

Identify the Acid Structures and Conjugate Bases

The given molecules are CH3COOH (acetic acid) and CCl3COOH (trichloroacetic acid). Remove an acidic proton (H+) from each to get the conjugate bases CH3COO- and CCl3COO- respectively.
02

Analyze the Effects of Electron Withdrawing Halogen

Now look at the structure of the conjugate bases. The negatively charged oxygen is part of the carboxyl group in both molecules. However, CCl3COO- has three chlorine atoms that are more electronegative than the hydrogen atoms in CH3COO-. This means they pull electron density towards themselves, helping to disperse (or 'delocalise') the negative charge on the oxygen atom in the conjugate base.
03

Identifying the Stronger Acid

Acid strength increases with the stability of its conjugate base. In this case, the conjugate base of CCl3COOH is more stable due to the electron-withdrawing effect of the chlorine atoms. This ultimately makes CCl3COOH a stronger acid than CH3COOH.

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Most popular questions from this chapter

What structural feature accounts for the decrease in the partial charge on the acidic hydrogen in the series HOCl, HOBr, HOI?

The H-X bond strength decreases in the series HF, HCl, HBr, HI. Explain this in terms of the molecular structure of the molecules.

Why does the partial charge on the acidic hydrogen increase in the series \(\mathrm{CH}_{3} \mathrm{COOH}, \mathrm{CH}_{2} \mathrm{ClCOOH}, \mathrm{CHCl}_{2} \mathrm{COOH}, \mathrm{CCl}_{3} \mathrm{COOH} ?\)

Which hydrogen atom is the most acidic hydrogen atom in HCOOH?

Predict which is most likely to be the stronger acid: \(\mathrm{H}_{2} \mathrm{O}\) or \(\mathrm{H}_{2} \mathrm{~S} .\) Explain your reasoning.
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