3. Acids and Bases

Use curved arrows to show the movement of electrons in the following reaction steps

a.

b.

We discuss the following reactions in subsequent chapters. Given the mechanisms shown, draw the mechanism of the reverse reaction.

(a)

We discuss the following reactions in subsequent chapters. Given the mechanisms shown, draw the mechanism of the reverse reaction.

(b)

Use curved arrows to show the flow of electrons that occurs in each step of the following mechanism

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

a.

The following reaction steps are shown using conventional electron pushing. (b) Use the bouncing arrow formalism to illustrate the formation of only the product shown.

(c)

Predict the product that results from the following 'pushed electrons.'

(a)

Predict the product that results from the following 'pushed electrons.'

(c)

Predict the product that results from the following 'pushed electrons.'

(f)

Predict the product that results from the following 'pushed electrons.'

(i)

The following reaction steps are shown using conventional electron pushing. (a) Draw the second product whose formation would have been rationalized with this same arrow.

(c)

Why are NH₃ and CH₃NH₂ no longer nucleophiles when they are protonated?

In each case, circle the stronger nucleophile.

(d)

We show in Chapter 20 that α , β-unsaturated ketones are electrophilic at C₄. Rationalize this observation.

In each case, circle the stronger nucleophile.

(c)