An organic lab student carried out the reaction of methylmagnesium iodide with acetone(CH3COCH3), followed by hydrolysis. During the distillation to isolate the product, she forgot to mark the vials she usedto collect the fractions. She turned in a product of formula C4H10O that boiled at 35 °C. The IR spectrum showed onlya weak O¬H stretch around 3300 cm-1, and the mass spectrum showed a base peak at m>z 59. The NMR spectrumshowed a quartet (J = 7 Hz) of area 2 at d 3.5 and a triplet (J = 7 Hz) of area 3 at d 1.3. Propose a structure for thisproduct, explain how it corresponds to the observed spectra, and suggest how the student isolated this compound.

An organic lab student carried out the reaction of methylmagnesium iodide with acetone(CH3COCH3), followed by hydrolysis. During the distillation to isolate the product, she forgot to mark the vials she usedto collect the fractions. She turned in a product of formula C4H10O that boiled at 35 °C. The IR spectrum showed onlya weak O¬H stretch around 3300 cm-1, and the mass spectrum showed a base peak at m>z 59. The NMR spectrumshowed a quartet (J = 7 Hz) of area 2 at d 3.5 and a triplet (J = 7 Hz) of area 3 at d 1.3. Propose a structure for thisproduct, explain how it corresponds to the observed spectra, and suggest how the student isolated this compound.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter12: Structure Determination: Mass Spectrometry And Infrared Spectroscopy

Section12.SE: Something Extra

Problem 47AP: Nitriles, Râ€“=Câ‰¡N, undergo a hydrolysis reaction when heated with aqueous acid. What is the...

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