(Another true story.) An organic lab student carried out the reaction of methylmagnesium iodide with acetone followed...

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

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Organic Chemistry

ISBN: 978-0321768414

8th edition

Authors: L. G. Wade Jr.

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