3. Acids and Bases

Would the following reactions go to the right or the left? Draw the products and label ALL species. Provide the full mechanism.

Which of the following compounds is the most acidic?

Arrange the following compounds in order of increasing Brønsted acidity: $\mathrm{CH}{3}_3\mathrm{COH}$, $\mathrm{CH}{3}_3\mathrm{COOH}$, $\mathrm{CH}{3}_3\mathrm{CH}{2}_2\mathrm{COOH}$, $\mathrm{CH}{3}_3\mathrm{CH}{2}_2\mathrm{OH}$.

Given the following compounds: ${\mathrm{CH}3}_1\mathrm{COOH}$ (acetic acid), ${\mathrm{CH}3}_1\mathrm{OH}$ (methanol), and $H_{2}O$ (water), rank them in order of increasing acidity.

Given the following compounds, which of the indicated protons is most acidic? (A) ${\mathrm{CH}}_3\mathrm{COOH}$ (B) ${\mathrm{CH}}_3\mathrm{OH}$ (C) ${\mathrm{CH}}_3\mathrm{NH}2$ (D) ${\mathrm{CH}}_4$

Given the following compounds: $\mathrm{NH}{3}_{}$ (ammonia), $\mathrm{CH}{3}_{}\mathrm{NH}{2}_{}$ (methylamine), and $\mathrm{NH}{2}_{}\mathrm{OH}$ (hydroxylamine), rank them in order of increasing basicity.

Which of the following molecules has the most acidic hydrogen atoms?

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

Arrange the following compounds in order of increasing acidity: $\mathrm{CH}{3}_2\mathrm{CH}-\mathrm{OH}$, $\mathrm{CH}{3}_3\mathrm{COH}$, $\mathrm{CH}{3}_2\mathrm{COOH}$.

Which is the most acidic proton in the following compound: ${\mathrm{CH}}_3\mathrm{COOH}$?

Would the following reactions go to the right or the left? Draw the products and label ALL species. Provide the full mechanism.

Arrange the following phenolic compounds in order of increasing acidity: $\mathrm{phenol}$, $p-\mathrm{nitrophenol}$, and $p-\mathrm{methoxyphenol}$.

Rank the following compounds in order of increasing acidity: $\mathrm{CH}{3}_3\mathrm{CH}\mathrm{OH}$, $\mathrm{CH}{3}_2\mathrm{CHOH}$, $\mathrm{CH}{3}_3\mathrm{COH}$.

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