3. Acids and Bases

Which species in each of the pairs in Problem 80 is the stronger base?

a.

b.

Given the following compounds: ${\mathrm{CH}}_3{\mathrm{CH}}_3\mathrm{COOH}$ (acetic acid), ${\mathrm{CH}}_3{\mathrm{CH}}_3{\mathrm{CH}}_3\mathrm{COH}$ (tert-butanol), and ${\mathrm{CH}}_3{\mathrm{CH}}_3\mathrm{NH}$ (dimethylamine), rank them from most acidic to least acidic.

Which of the following correctly ranks the compounds $\mathrm{CH}{3}_3\mathrm{COH}$, $\mathrm{CH}{3}_2\mathrm{COH}$, and $\mathrm{CH}{3}_1\mathrm{COH}$ in order of decreasing electrophilic strength (most electrophilic to least electrophilic)?

Which of the following compounds contains the most acidic hydrogen atom?

Explain why the pK_a of p-nitrophenol is 7.14, whereas the pK_a of m-nitrophenol is 8.39.

In the compound ${\mathrm{CH}}_3{\mathrm{COCH}}_2\mathrm{COOH}$ (acetoacetic acid), which hydrogen is the most acidic?

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

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

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

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

All of the following compounds can react as acids. Without using a table of acidities, rank them in order of increasing acidity. Explain your ranking.

a. CH₃CH₂SO₃H

b. CH₃CH₂OH

c. CH₃CH₂COOH

d. CH₃CHClCOOH

e. ClCH₂CH₂COOH

Rank the following species in order of increasing acidity. Explain your reasons for ordering them as you do.

HF NH₃ H₂SO₄ CH₃OH CH₃COOH H₃O⁺ H₂O

Methyllithium (CH₃Li) is often used as a base in organic reactions.

b. What is the conjugate acid of CH₃Li? Would you expect CH₃Li to be a strong base or a weak base?