3. Acids and Bases

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?

Rank the ions (⁻CH₃, ⁻NH₂, HO⁻, and F⁻) from most basic to least basic.

Rank the following alcohols from strongest to weakest acid.

CH₂═CHCH₂OH; CH₃CH₂CH₂OH; HC≡CCH₂OH

Rank the following compounds from strongest to weakest acid:

CH₃CH₂OH; CH₃CH₂NH₂; CH₃CH₂SH; CH₃CH₂CH₃

If HCl is a weaker acid than HBr, why is ClCH₂COOH a stronger acid than BrCH₂COOH?

Which is a stronger base?

a.

b.