Each of these compounds can react as a nucleophile. In each case, use curved arrows to show how the nucleophile would react with the strong electrophile BF₃.
(f) (CH₃)₂S

Identify the electrophile and the nucleophile in each of the following reaction steps and then draw curved arrows to illustrate the bond-making and bondbreaking processes.

c.

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.

i.

In each reaction, label the reactants as Lewis acids (electrophiles) or Lewis bases (nucleophiles). Use curved arrows to show the movement of electron pairs in the reactions. Draw any nonbonding electrons to show how they participate in the reactions.

c.

Each of these compounds can react as a nucleophile. In each case, use curved arrows to show how the nucleophile would react with the strong electrophile BF₃.

(e) CH₃CH₂OH

Which atoms in the enol ether would you expect to react with Br⁺ ?

To which atom of formaldehyde would you expect H⁺ to add?

For practice in recognizing mechanisms, classify each reaction according to the type of mechanism you expect:

1. Free-radical chain reaction

2. Reaction involving strong bases and strong nucleophiles

3. Reaction involving strong acids and strong electrophiles

(b)

For practice in recognizing mechanisms, classify each reaction according to the type of mechanism you expect:

1. Free-radical chain reaction

2. Reaction involving strong bases and strong nucleophiles

3. Reaction involving strong acids and strong electrophiles

(a)