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.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter23: Carbonyl Condensation Reactions

Section23.SE: Something Extra

Problem 73AP

See similar textbooks

Similar questions

Treatment of an aldehyde or ketone with cyanide ion (-:C=N), followed by protonation of the tetrahedral alkoxide ion intermediate, gives a cyanohydrin. Show the structure of the cyanohydrin obtained from cyclohexanone.
Why do you suppose ketone halogenations in acidic media are referred to as being acid-catalyzed, whereas halogenations in basic media are base-promoted? In other words, why is a full equivalent of base required for halogenation?
Devise a synthesis of the ketone hexan-3-one, CH3CH2COCH2CH2CH3, from CH3CH2Br as the only organic starting material; that is, all the carbon atoms in hexan-3-one must come from CH3CH2Br. You may use any other neededreagents.
a) Write out the first 3 steps only(to the tetrahedral intermediate shown) in the 6-step arrow pushing mechanism showing how ethyl propanoate is hydrolyzed in acid to form propanoic acidand ethanol. b) NaOH/H2O also serveto hydrolyze an ester; briefly explain why NaOH/H2Ois generally preferable.
Draw a stepwise mechanism for the conversion of lactone C to carboxylic acid D. C is a key intermediate in the synthesis of prostaglandins (Section 19.6) by Nobel Laureate E. J. Corey and co-workers at Harvard University.
Esters with only one α hydrogen generally give poor yields in the Claisen condensation. Q: Propose a mechanism for the Claisen condensation of ethyl isobutyrate.
plese quickly thanks ! 4. Please write out the equation to the synthesis of Ethyl Acetate. Since this reaction is reversible, how to drive an esterification toward completion. How to work up after the reaction completion and explain the use for every workup.
Chemistry Draw the product formed when phenylacetaldehyde (C6H5CH2CHO) is treated with reach reagent: f. (CH3)2CHNH2, mild acid g. (CH3CH2)2NH, mild acid h. CH3CH2OH (excess), H+ i. piperidine, mild acid j. HOCH2CH2OH, H+
Draw the product formed when phenylacetic acid (C6H5CH2COOH) istreated with following reagent. With some reagents, no reaction occurs. [1] SOCl2; [2] CH3CH2CH2NH2 (excess)
2-Pentylcinnamaldehyde, commonly called flosal, is a perfume ingredient with a jasminelike odor. Flosal is an α,β-unsaturated aldehyde made by a crossed aldol reactionbetween benzaldehyde (C6H5CHO) and heptanal (CH3CH2CH2CH2CH2CH2CHO), followed by dehydration. Draw a stepwise mechanism for the following reaction that prepares flosal.
H8. In the partial reduction by NaBH4 of HPK (Hajos-Parrish ketone), the reaction proceeds only to one of the ketones, and the reagent approaches from one of its carbonyl planes, and therefore only one alcohol is selectively obtained. Draw all compounds that can be generated by NaBH4 reduction and explain why the reaction has proceeded selectively.
Draw the product formed when phenylacetic acid (C6H5CH2COOH) istreated with following reagent. With some reagents, no reaction occurs. SOCl2