3. Acids and Bases

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?

Given the following compounds: ${\mathrm{CH}}_3{\mathrm{COH}}_3$ (tert-butanol), ${\mathrm{CH}}_3{\mathrm{CHOH}}_2$ (isopropanol), and ${\mathrm{CH}}_3{\mathrm{CH}}_2\mathrm{OH}$ (ethanol), arrange them in order of decreasing $\mathrm{pK}a$ (highest $\mathrm{pK}a$ first).

Which of the following compounds is most acidic?

Given the following solutions: ${\mathrm{CH}}_3\mathrm{COOH}$ (acetic acid), $\mathrm{HCl}$ (hydrochloric acid), and $\mathrm{NH}{4}_{\mathrm{+}}$ (ammonium ion), rank them in order of increasing acidity.

Given the compound ${\mathrm{CH}}_3\mathrm{COOH}$ (acetic acid), identify the most acidic proton.

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

Given the following compounds with bolded hydrogens: (A) ${\mathrm{CH}}_3{\mathrm{CH}}_{2}OH$ (bold H on the OH), (B) ${\mathrm{CH}}_3\mathrm{COO}H$ (bold H on the COOH), and (C) ${\mathrm{CH}}_{3}NH{2}_{}$ (bold H on the NH$2_{}$), rank the bolded hydrogens in order of increasing acidity.

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

Which is a stronger acid?

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d. CH₃CH₂CH₂OH or CH₃CH₂CH₂SH

Given the following compounds: ${\mathrm{CH}}_3\mathrm{COOH}$, ${\mathrm{CH}}_3\mathrm{OH}$, and ${\mathrm{NH}}_3$, rank them in order of decreasing acidity.

Which acid in each pair would you expect to more readily donate a proton to a basic compound?

(b)