Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
Bartleby Related Questions Icon

Related questions

Question
**Problem Statement:**

Why can you NOT prepare the following compound using either the malonic ester synthesis or the acetoacetic ester synthesis?

**Chemical Structure:**

The image depicts a ketone structure with the carbonyl group (C=O) attached to a methyl group on one side and a phenyl group (Ph) on the other. This represents acetophenone.

**Explanation:**

In malonic ester synthesis and acetoacetic ester synthesis, the methods involve forming a substituted carboxylic acid or a β-keto ester, respectively. Both processes typically rely on forming a carbanion adjacent to the ester group, followed by alkylation.

- **Malonic Ester Synthesis** usually forms carboxylic acids after hydrolysis and decarboxylation, and it can't introduce a phenyl group directly onto the β-carbon of the ester.

- **Acetoacetic Ester Synthesis** involves the production of ketones, but it similarly struggles to introduce complex aryl groups like phenyl directly via the standard nucleophilic substitution routes typical to these syntheses.

Therefore, due to the limitations in introducing a phenyl substituent via these syntheses, acetophenone cannot be readily prepared using these methods.
expand button
Transcribed Image Text:**Problem Statement:** Why can you NOT prepare the following compound using either the malonic ester synthesis or the acetoacetic ester synthesis? **Chemical Structure:** The image depicts a ketone structure with the carbonyl group (C=O) attached to a methyl group on one side and a phenyl group (Ph) on the other. This represents acetophenone. **Explanation:** In malonic ester synthesis and acetoacetic ester synthesis, the methods involve forming a substituted carboxylic acid or a β-keto ester, respectively. Both processes typically rely on forming a carbanion adjacent to the ester group, followed by alkylation. - **Malonic Ester Synthesis** usually forms carboxylic acids after hydrolysis and decarboxylation, and it can't introduce a phenyl group directly onto the β-carbon of the ester. - **Acetoacetic Ester Synthesis** involves the production of ketones, but it similarly struggles to introduce complex aryl groups like phenyl directly via the standard nucleophilic substitution routes typical to these syntheses. Therefore, due to the limitations in introducing a phenyl substituent via these syntheses, acetophenone cannot be readily prepared using these methods.
Expert Solution
Check Mark
Knowledge Booster
Background pattern image
Chemistry
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
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY