Ethanol, methylamine, and acetic acid are all amphoteric, reacting as either acids or bases depending on the conditions.

b. Rank ethanol, methylamine, and acetic acid in decreasing order of basicity. In each case, show the equation for the reaction with a generic acid (HA) to give the conjugate acid.

The following compounds can all react as acids.

c. Rank the original compounds in order, from strongest acid to weakest acid.

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!)

Consider each pair of bases, and explain which one is more basic. Draw their conjugate acids, and show which one is a stronger acid.

(a)

(b)

Write equations for the following acid–base reactions. Label the conjugate acids and bases, and show any inductive stabilization. Predict whether the equilibrium favors the reactants or products. Try to do this without using a table of pKa values, but if you need a hint, you can consult Appendix 4.

a. CH₃CH₂OH + CH₃NH⁻

b. F₃CCOONa + Br₃C—COOH

c. CH₃OH + H₂SO₄

Ethanol, methylamine, and acetic acid are all amphoteric, reacting as either acids or bases depending on the conditions.

a. Rank ethanol, methylamine, and acetic acid in decreasing order of acidity. In each case, show the equation for the reaction with a generic base (B:⁻) to give the conjugate base.

Which is a stronger acid?

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d. CH₃CH₂CH₂OH or CH₃CH₂CH₂SH

Which is a stronger acid?

For each of the following compounds, indicate the atom that is protonated when an acid is added to a solution of the compound.

c.

d.