Rank the following original compounds in order from strongest base to weakest base.

Ethaneperoxoic acid, C₂H₄O₃, has a pK_a value of 8.20. It is a weaker acid when compared to ethanoic acid, C₂H₄O₂ (pK_a = 4.74). Why is ethaneperoxoic acid weaker than ethanoic acid in terms of acidity?

Given the structure of 2-ethyl-2,5,5-trimethylpyrrolidin-1-ide, show its conjugate acid and choose the pK _a value from the table that could help predict the stability of the base.

Use the K_eq values stated in each of the following equations to determine the factor by which cyanomethanide is a stronger base than pyrrolide.

Which of the bases given below are able to deprotonate propanoic acid (pK_a = 4.88) in an acid-base reaction that favors the formation of products?
(i) CH₃O⁻ (pK_a of CH₃OH = 15.9)
(ii) NH₃ (pK_a of NH₄⁺ = 9.4)
(iii) CH₃C≡C⁻ (pK_a of CH₃C≡CH = 25)
(iv) CH₃CH₂OH (pK_a of CH₃CH₂OH₂⁺ = −2.5)
(v) H₂O (pK_a of H₃O⁺ = −1.7)
(vi) Br⁻ (pK_a of HBr = −9)

Complete the following acid-base reactions and predict the equilibrium positions of these reactions using the information given in the table.

a. CH₃OH + NaNH₂
b. ⁻CN + CH₃COOH
c. CH₃CH₂OH + HCOO⁻

Rank these compounds in order of increasing acidity.

A. CH₃CH₃

B. CH₃OH

C. CH₃NH₂

D. CH₃SH

Identify the stronger acid in each of the following pairs.

A negative charge on an adjacent carbon atom can be stabilized by a nitrile group (-CN) through resonance. Of the three hydroxybenzonitrile derivatives shown below, one is only slightly more acidic than phenol, while the other two are much more acidic than phenol. Use resonance structures of the appropriate phenoxide ions to explain why two of the ions are unusually stable.