Macroscale and Microscale Organic Experiments
7th Edition
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Kenneth L. Williamson, Katherine M. Masters
Chapter45: Synthesis And Bioassay Of Sulfanilamide And Derivatives
Section: Chapter Questions
Problem 5Q
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Treatment of isobutene [(CH3)2C=CH2] with (CH3)3CLi forms a carbanion that reacts with CH2=O to form H after water is added to the reaction mixture. H has a molecular ion in its mass spectrum at m/z = 86, and shows fragments at 71 and 68. H exhibits absorptions in its IR spectrum at 3600−3200 and 1651 cm−1, and has the 1H NMR spectrum given below. What is the structure of H?
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