3. Acids and Bases

Which of the following indicated atoms would you expect to be most basic?

(b)

Which is a stronger acid?

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d. CH₃CH₂CH₂OH or CH₃CH₂CH₂SH

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

(b)

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

a.

b.

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

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.