a) Ketoacid Z below can be synthesized from ethyl acetoacetate W via an acetoacetic ester synthesis. The B-ketoester W can be initially synthesized by Claisen condensation reaction of ester V. NaOEt NaOEt Base Ester V OEt CH,Br OEt | HO CH, Ketoacid Z i) Identify the structure of ester V. ii) Transformation of W to X and X to Y are alkylation reactions. Draw the structures of the intermediates X and Y. Determine a suitable base for the conversion of X to Y. iii) With regards to the formation of the ketoacid Z from Y, show the steps involved in the reaction by giving the appropriate intermediates, reagents and reaction conditions. iv) Explain why only one of the carbonyl groups in Y is lost as carbon dioxide gas.

a) Ketoacid Z below can be synthesized from ethyl acetoacetate W via an acetoacetic ester synthesis. The B-ketoester W can be initially synthesized by Claisen condensation reaction of ester V. NaOEt NaOEt Base Ester V OEt CH,Br OEt | HO CH, Ketoacid Z i) Identify the structure of ester V. ii) Transformation of W to X and X to Y are alkylation reactions. Draw the structures of the intermediates X and Y. Determine a suitable base for the conversion of X to Y. iii) With regards to the formation of the ketoacid Z from Y, show the steps involved in the reaction by giving the appropriate intermediates, reagents and reaction conditions. iv) Explain why only one of the carbonyl groups in Y is lost as carbon dioxide gas.

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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Question

a) Ketoacid Z below can be synthesized from ethyl acetoacetate W via an acetoacetic ester
synthesis. The B-ketoester W can be initially synthesized by Claisen condensation reaction
of ester V.
NaOEt
NaOEt
Base
Ester V
OEt
CH,Br
OEt
|
HO
CH,
Ketoacid Z
i) Identify the structure of ester V.
ii) Transformation of W to X and X to Y are alkylation reactions. Draw the structures of
the intermediates X and Y. Determine a suitable base for the conversion of X to Y.
iii) With regards to the formation of the ketoacid Z from Y, show the steps involved in the
reaction by giving the appropriate intermediates, reagents and reaction conditions.
iv) Explain why only one of the carbonyl groups in Y is lost as carbon dioxide gas.

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