Reaction Mechanism Practice Problems

Use curved arrows to show how the following nucleophiles react with the strong electrophile nitrosonium ion (NO⁺).

a. CH₃CH₂NH₂
b. CH₃O⁻

Use curved arrows to show how the following electrophiles react with the strong nucleophile sodium methoxide (CH₃O⁻Na⁺).

a. BF₃
b. CH₃I

Use curved arrows to show how the following electrophiles react with the strong nucleophile sodium methoxide (CH₃O⁻Na⁺).

Identify the reactants as Lewis acid (electrophile) and Lewis base (nucleophile) in the following reaction:

Indicate participating nonbonding electrons and draw curved arrows to describe how electrons move in this reaction.

Identify the reactants as Lewis acid (electrophile) and Lewis base (nucleophile) in the following reaction:

Indicate participating nonbonding electrons and draw curved arrows to describe how electrons move in this reaction.

Consider the following reaction:

Identify the Lewis acid (electrophile) and Lewis base (nucleophile) in these reactions and draw curved arrows to indicate the flow of electrons.

Consider the following reaction:

Identify the Lewis acid (electrophile) and Lewis base (nucleophile) in these reactions and draw curved arrows to indicate the flow of electrons.

Consider the following reaction:

Identify the Lewis acid (electrophile) and Lewis base (nucleophile) in these reactions and draw curved arrows to indicate the flow of electrons.

Draw the arrow-pushing mechanism to show the product formation in the following reaction.

For the given reaction, draw a mechanism and a reaction coordinate diagram.

For the given acid-base reaction, draw an arrow-pushing mechanism and a reaction coordinate diagram.

Provide a suitable arrow-pushing mechanism for the reaction given below.

Refer to the structure of (E)-hept-3-en-2-one, an α,β-unsaturated ketone. The compound is electrophilic at C ₂ and C₄. Explain why this is so. 

Which one is the stronger nucleophile among the following?

Identify the below-given molecule as an electrophile or a nucleophile. Provide a reason.

Identify the below-given molecule as an electrophile or a nucleophile. Justify your answer.

Identify the reactants as nucleophile and electrophile in the reaction given below.

Which of the following is a stronger nucleophile?

Draw the arrow-pushing mechanism to show the bond breaking in the following reaction.

Draw the arrow-pushing mechanism to show the formation of the following product from the given reactants.

Draw the arrow-pushing mechanism to show the formation of the following product from the given reactants. Hint: The mechanism would require three arrows.

Determine the type of each of the arrows displayed in the following arrow-pushing mechanism.

Type I: nucleophilic attack by a lone pair of electrons

Type II: heterolytic cleavage of a σ bond

Type III: nucleophilic attack by the π electrons

Type IV: dissociation of a π bond

Type V: formation of a π bond

Determine the type of each of the arrows marked in the following arrow-pushing mechanism.

Type I: nucleophilic attack by a lone pair of electrons

Type II: heterolytic cleavage of a σ bond

Type III: nucleophilic attack by the π electrons

Type IV: dissociation of a π bond

Type V: formation of a π bond

The following reaction mechanism shows the conversion of an alkyl bromide into an alcohol. Draw the mechanism for the backward reaction.

Predict the products expected from the electron pushing shown in the below-given compound.

What product(s) are expected from the following 'electron pushing'?

What product(s) are expected from the following arrow-pushing formalism?

What product(s) are expected from the following arrow-pushing formalism shown below?

The following reaction is described using the arrow-pushing formalism, and only one of the two expected products is given. Draw the second product that is expected to be formed as a result of this electron pushing.

The following reaction is shown with the conventional arrow-pushing formalism. Show the formation of the given product using a more appropriate bouncing arrow formalism.

Show the movement of electrons in the given reactions using curved arrows.

Identify the electrophile and nucleophile in each of the reactions given below.

In each of the following reactions, indicate the electrophile and the nucleophile.

Show the flow of electrons in each step of the following mechanism using curved arrows.

Show the mechanism of the following reaction using curved arrows.

Why are the protonated (CH₃CH₂)₂NH and CH₃CH₂NH₂ no longer nucleophiles?

Show the movement of electrons in the given reaction using curved arrows and identify the electrophile and the nucleophile in it.