3. Acids and Bases

Given the following compounds: ${\mathrm{CH}3}_{}\mathrm{COOH}$ (acetic acid), ${\mathrm{CH}3}_{}\mathrm{OH}$ (methanol), ${\mathrm{CH}3}_{}N$ (ammonia), and ${\mathrm{CH}4}_{}$ (methane), rank them in order of decreasing acidity (most acidic first).

Given the following compounds: $\mathrm{CH}{3}_3\mathrm{COH}$ (tert-butanol), $\mathrm{CH}{3}_2\mathrm{COH}$ (isopropanol), and $\mathrm{CH}{3}_1\mathrm{COH}$ (ethanol), rank them in order of decreasing electrophile strength.

Which of the following compounds is the most acidic?

Rank the following compounds from highest oxidation level to lowest: $\mathrm{CH}{3}_3\mathrm{COH}$ (tert-butanol), $\mathrm{CH}{3}_3\mathrm{COOH}$ (pivalic acid), $\mathrm{CH}{3}_3\mathrm{COCH}{3}_3$ (pinacolone), and $\mathrm{CH}{3}_3\mathrm{CH}{3}_3$ (neopentane).

Given the following compounds: $\mathrm{CH}{3}_2\mathrm{CH}\mathrm{OH}$ (isopropanol), $\mathrm{CH}{3}_3\mathrm{COH}$ (tert-butanol), and $\mathrm{CH}{3}_2\mathrm{CO}\mathrm{OH}$ (acetic acid), arrange them in order of increasing acidity.

Which of the following compounds is the most acidic?

In the context of ranking acidity among substituted benzoic acids, which of the following substituents on the benzene ring increases the acidity of benzoic acid the most?

Given the following compounds, rank the bold-faced hydrogens from most acidic to least acidic: (1) ${\mathrm{CH}}_3\mathrm{COOH}$ (acetic acid), (2) ${\mathrm{CH}}_3\mathrm{OH}$ (methanol), (3) ${\mathrm{CH}}_4$ (methane).

Rank the following compounds in decreasing order of acidity: $\mathrm{CH}{3}_1\mathrm{COOH}$, $\mathrm{CH}{3}_1\mathrm{OH}$, $\mathrm{NH}{3}_1$, $\mathrm{CH}{4}_1$.

Given the following acids: $\mathrm{CH}{3}_3\mathrm{COOH}$ (acetic acid), $\mathrm{HCl}$ (hydrochloric acid), and $\mathrm{CH}{3}_3\mathrm{OH}$ (methanol), rank them from lowest $\mathrm{pK}a$ to highest $\mathrm{pK}a$.

Which of the following carboxylic acids is the most acidic?

Given the following compounds: ${\mathrm{CH}}_3{3}_{3}N$ (trimethylamine), ${\mathrm{NH}}_3$ (ammonia), and ${\mathrm{CH}}_3{2}_2\mathrm{NH}$ (dimethylamine), rank them in order of increasing basicity.

Which of the following four compounds is the most acidic (i.e., has the lowest $pKa$ value)?

Given the following compounds: $\mathrm{CH}{3}_2\mathrm{NH}$, $\mathrm{CH}{3}_{3}N$, $\mathrm{NH}{2}_2$, and $\mathrm{NH}3$, rank them in order of decreasing base strength (from strongest base to weakest base).

Rank the following carbon-centered radicals in order of increasing stability: methyl radical (${\mathrm{CH}}_3\cdot$), primary radical (${\mathrm{CH}}_3{\mathrm{CH}}_2\cdot$), secondary radical (${\mathrm{CH}}_3{\mathrm{CH}}_2{\mathrm{CH}}_2\cdot$), and tertiary radical (${\mathrm{CH}}_3{C}_3\cdot$). Which sequence correctly orders them from least to most stable?