2. Draw the mechanism of the base-catalyzed aldol condensation reaction of two molecules of acetone using the arrow formalism.

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...
icon
Related questions
icon
Concept explainers
Question
**Exercise 2: Aldol Condensation Mechanism**

**Task:** Draw the mechanism of the base-catalyzed aldol condensation reaction of two molecules of acetone using the arrow formalism.

---

**Explanation:**
In this exercise, you are required to illustrate the step-by-step mechanism of the aldol condensation reaction facilitated by a base catalyst. The reaction involves two acetone molecules and you will use the arrow formalism to demonstrate how electrons are transferred during the reaction.

When constructing your diagram, ensure that each step highlights the shifts in electron density and formation of bonds:

1. **Enolate Ion Formation:** Demonstrate the abstraction of an alpha hydrogen from one acetone molecule by the base, leading to the formation of an enolate ion.

2. **Nucleophilic Addition:** Show how the enolate ion attacks the carbonyl carbon of a second acetone molecule.

3. **Formation of Beta-Hydroxy Ketone:** Highlight the resulting beta-hydroxy ketone formation.

4. **Dehydration:** Illustrate the elimination step where water is expelled, leading to the formation of the alpha, beta-unsaturated ketone product.

Remember to ensure clarity in your arrow notation to effectively communicate each mechanistic step.
Transcribed Image Text:**Exercise 2: Aldol Condensation Mechanism** **Task:** Draw the mechanism of the base-catalyzed aldol condensation reaction of two molecules of acetone using the arrow formalism. --- **Explanation:** In this exercise, you are required to illustrate the step-by-step mechanism of the aldol condensation reaction facilitated by a base catalyst. The reaction involves two acetone molecules and you will use the arrow formalism to demonstrate how electrons are transferred during the reaction. When constructing your diagram, ensure that each step highlights the shifts in electron density and formation of bonds: 1. **Enolate Ion Formation:** Demonstrate the abstraction of an alpha hydrogen from one acetone molecule by the base, leading to the formation of an enolate ion. 2. **Nucleophilic Addition:** Show how the enolate ion attacks the carbonyl carbon of a second acetone molecule. 3. **Formation of Beta-Hydroxy Ketone:** Highlight the resulting beta-hydroxy ketone formation. 4. **Dehydration:** Illustrate the elimination step where water is expelled, leading to the formation of the alpha, beta-unsaturated ketone product. Remember to ensure clarity in your arrow notation to effectively communicate each mechanistic step.
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Catalysis and Enzymatic Reactions
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY