Provide the reaction mechanism for this reaction and identify the final product. OEt NaOEt, EtOH

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
Question

Question attached

Provide the reaction mechanism for this reaction and identify the final product.
OEt
NaOEt, EtOH
Transcribed Image Text:Provide the reaction mechanism for this reaction and identify the final product. OEt NaOEt, EtOH
Expert Solution
Step 1

The given reaction is an example of the claisen condensation reaction which results in the formation of a beta-keto ester.

In the given reaction the two esters present are ethyl benzoate and ethyl butanoate. The ethyl benzoate does not consists of any hydrogen atom present at the alpha carbon of the carbonyl group, while there are two hydrogen atoms present on the alpha carbon of the carbonyl group in ethyl butanoate. So the first step of the reaction mechanism involves the abstraction of one of the hydrogen presents on the alpha carbon by the base NaOEt whic results in the formation of a carbanion. 

 

Chemistry homework question answer, step 1, image 1

Step 2

In the next step, the carbanion formed will act as a nucleophile and attacks on the carbonyl carbon of the ethyl benzoate followed by the removal of EtO- to form a beta-keto ester. 

Chemistry homework question answer, step 2, image 1

 

steps

Step by step

Solved in 3 steps with 3 images

Blurred answer
Knowledge Booster
Introduction to 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
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