We will use trimethyl phosphonoacetate as the ylide precurser in this experiment. The ylide is generated by deprotonation at the carbon alpha to the carbonyl (between the carbonyl and the phosphonate ester). Draw appropriate resonance structures for this ylide. State whether the ylide is classified as a stabilized or an unstabilized ylide

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter14: Elimination

Section: Chapter Questions

Problem 35CTQ

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Question

We will use trimethyl phosphonoacetate as the ylide precurser in this experiment. The ylide is generated by deprotonation at the carbon alpha to the carbonyl (between the carbonyl and the phosphonate ester). Draw appropriate resonance structures for this ylide. State whether the ylide is classified as a stabilized or an unstabilized ylide. Predict the likely major and minor products of the reaction with benzaldehyde based upon the nature of the ylide. Rationalizing why the ylide classes produce different stereoisomers is beyond the scope of this course and will not be assessed for credit

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