3. Acids and Bases

Rank the following compounds in order of increasing acidity: $\mathrm{CH}{3}_3\mathrm{CH}\mathrm{OH}$, $\mathrm{CH}{3}_3\mathrm{COOH}$, $\mathrm{CH}{3}_3\mathrm{NH}2$.

Consider the type of orbitals involved, and rank the following nitrogen compounds in order of decreasing basicity. 2. Rank the conjugate acids in order of increasing acidity. (Hint: These two orders should be the same!)

Given the molecule ${\mathrm{CH}}_3{\mathrm{CO}}_{2}H$ (acetic acid), select the most acidic type of hydrogen in this molecule.

Given the following compounds: $\mathrm{CH}{3}_{}3\mathrm{COH}$ (tert-butanol), $\mathrm{CH}{3}_{}2\mathrm{CHOH}$ (isopropanol), and $\mathrm{CH}{3}_{}3\mathrm{COOH}$ (pivalic acid), rank them in order of increasing acidity.

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).

Identify the stronger base in each pair. Explain your choice. Citing pK_a values is not an acceptable answer.

(d)

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 $\mathrm{pK}a$.