When but-2-enal is treated with 3-phenylpropenal in the presence of a strong base, a compound is formed whose formula is C13H12O. In its 1H NMR spectrum, one signal has a chemical shift around 10 ppm, several overlapping signals have chemical shifts between 7 and 9 ppm, and several other overlapping signals have chemical shifts between 5 and 6 ppm. Integration of those sets of signals gives a 1∶5∶6 ratio.(a) What is the structure of the product?(b) Draw a complete, detailed mechanism that accounts for the formation of the product.

When but-2-enal is treated with 3-phenylpropenal in the presence of a strong base, a compound is formed whose formula is C13H12O. In its 1H NMR spectrum, one signal has a chemical shift around 10 ppm, several overlapping signals have chemical shifts between 7 and 9 ppm, and several other overlapping signals have chemical shifts between 5 and 6 ppm. Integration of those sets of signals gives a 1∶5∶6 ratio.(a) What is the structure of the product?(b) Draw a complete, detailed mechanism that accounts for the formation of the product.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter13: Nuclear Magnetic Resonance Spectroscopy

Section: Chapter Questions

Problem 13.17P: Following are 1H-NMR spectra for compounds G, H, and I, each with the molecular formula C5H12O. Each...

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