c) Answer ALL parts (i) to (v)- (!) (i) Draw the structure of th of the ester 4 by the bas (ii) Suggest a mechanism f its reaction with ethanc (iii) For each diastereoisom conformations (4 chair (iv) By referring to your ch diastereoisomer (4 or 6 been reached. (v) What do you think the performed using NaOM NaOEt O H OEt HO. Me 4.

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
(c) Answer ALL parts (i) to (v).
(i) Draw the structure of the enolate ion 5 formed by deprotonation
of the ester 4 by the base NaOEt.
(ii) Suggest a mechanism for the formation of the enolate 5 and for
its reaction with ethanol to produce the diastereoisomeric ester 6.
(iii) For each diastereoisomer (4 and 6) draw the two chair
conformations (4 chair diagrams in total).
(iv) By referring to your chair diagrams, predict which
diastereoisomer (4 or 6) will predominate when equilibrium has
been reached.
(v) What do you think the result would be if the reaction was instead
performed using NaOMe in MeOH?
NaOEt
O H
он
OEt
OEt
Ме.
Me
Ме
Ме.
Me-
Me
4.
9
Transcribed Image Text:(c) Answer ALL parts (i) to (v). (i) Draw the structure of the enolate ion 5 formed by deprotonation of the ester 4 by the base NaOEt. (ii) Suggest a mechanism for the formation of the enolate 5 and for its reaction with ethanol to produce the diastereoisomeric ester 6. (iii) For each diastereoisomer (4 and 6) draw the two chair conformations (4 chair diagrams in total). (iv) By referring to your chair diagrams, predict which diastereoisomer (4 or 6) will predominate when equilibrium has been reached. (v) What do you think the result would be if the reaction was instead performed using NaOMe in MeOH? NaOEt O H он OEt OEt Ме. Me Ме Ме. Me- Me 4. 9
Expert Solution
steps

Step by step

Solved in 2 steps with 2 images

Blurred answer
Knowledge Booster
Carboxylic Acids and their Derivatives
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.
Similar questions
  • SEE MORE QUESTIONS
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