The following compounds can all react as acids.

a. For each compound, show its conjugate base. Show any resonance forms if applicable. b. Rank the conjugate bases in the order you would predict, from most stable to least stable.

Predict the products of the following acid–base reactions.

(c)

(d)

Predict the products of the following acid–base reactions.

(a) H₂SO₄ + CH₃COO^– ⇌

(b) CH₃COOH + (CH₃)₃N: ⇌

Label the reactants in these acid–base reactions as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions.

(c)

In the following acid–base reactions,

1. draw Lewis structures of the reactants and the products.

2. determine which species are acting as electrophiles (acids) and which are acting as nucleophiles (bases).

3. use the curved-arrow formalism to show the movement of electron pairs in these ­reactions, as well as the imaginary movement in the resonance hybrids of the products.

4. indicate which reactions are best termed Brønsted–Lowry acid–base reactions.

(a)

Ammonia appears in [TABLE 2-2 ] as both an acid and a conjugate base. a. Explain how ammonia can act as both an acid and a base. Which of these roles does it commonly fill in aqueous solutions?

b. Show how water can serve as both an acid and a base.

What products are formed when each of the following reacts with HO⁻?

a. CH₃OH

b. ⁺NH₄

Draw the products of the following reactions. Use curved arrows to show where the pair of electrons starts and where it ends up.

a.

b.

What products are formed when each of the following reacts with HO⁻?

e. ⁺CH₃

f. FeBr₃