In the reaction shown below draw curly arrows to show how the acetylide can act as a nucleophile. **Transcription and Diagram Explanation**This image depicts a chemical reaction mechanism involving an anionic alkyne and a ketone molecule, leading to the formation of an alkoxide intermediate.- **Reactants:** - On the left, the reactants include an alkyne anion (\( \text{H-C}\equiv\text{C}^- \)) and acetone (\( \text{(CH}_3\text{)_2C=O} \)).- **Reaction Step:** - The arrow indicates the progression of the reaction from the reactants to the products. - The alkyne anion attacks the electrophilic carbonyl carbon of the acetone, resulting in the formation of an alkoxide ion with the alkyne now attached.- **Intermediate:** - The intermediate formed is an alkoxide ion (\( \text{H-C}\equiv\text{C-C(O}^-)(CH}_3)_2 \)). - A water molecule (\( \text{H}_3\text{O}^+ \)) is also produced as a byproduct.- **Protonation Step:** - The alkoxide ion undergoes protonation, as indicated by the vertical arrow moving downward. - The oxygen atom with a negative charge (\( \text{O}^- \)) gains a proton, leading to the formation of an alcohol (\( \text{H-C}\equiv\text{C-C(OH)(CH}_3)_2 \)).This reaction mechanism is a classic example of a nucleophilic addition where the alkyne anion acts as a nucleophile, and the carbonyl carbon acts as an electrophile. This addition forms an alcohol when the alkoxide intermediate is protonated.

Answered: In the reaction shown below draw curly…

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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In the reaction shown below draw curly arrows to show how the acetylide can act as a nucleophile.

**Transcription and Diagram Explanation**

This image depicts a chemical reaction mechanism involving an anionic alkyne and a ketone molecule, leading to the formation of an alkoxide intermediate.

- **Reactants:**
- On the left, the reactants include an alkyne anion (\( \text{H-C}\equiv\text{C}^- \)) and acetone (\( \text{(CH}_3\text{)_2C=O} \)).

- **Reaction Step:**
- The arrow indicates the progression of the reaction from the reactants to the products.
- The alkyne anion attacks the electrophilic carbonyl carbon of the acetone, resulting in the formation of an alkoxide ion with the alkyne now attached.

- **Intermediate:**
- The intermediate formed is an alkoxide ion (\( \text{H-C}\equiv\text{C-C(O}^-)(CH}_3)_2 \)).
- A water molecule (\( \text{H}_3\text{O}^+ \)) is also produced as a byproduct.

- **Protonation Step:**
- The alkoxide ion undergoes protonation, as indicated by the vertical arrow moving downward.
- The oxygen atom with a negative charge (\( \text{O}^- \)) gains a proton, leading to the formation of an alcohol (\( \text{H-C}\equiv\text{C-C(OH)(CH}_3)_2 \)).

This reaction mechanism is a classic example of a nucleophilic addition where the alkyne anion acts as a nucleophile, and the carbonyl carbon acts as an electrophile. This addition forms an alcohol when the alkoxide intermediate is protonated.

Expert Solution

Step 1

The following steps are involved in the attack of acetylide as a nucleophile over acetone:

The movement of the electron density over oxygen in the carbonyl group of the acetone. Oxygen gains a partial negative charge and carbon gains a partial positive charge. The acetylide ion attacks the positive center of the carbonyl compound.
The hydronium attack attacks the oxygen atom which leads to the formation of hydroxyl group in the compound and water molecule.

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