Treatment of isobutene [(CH3)2C CH2] with (CH3)3CLi forms a carbanion that reacts with

Chapter 20, Problem 20.78

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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 36003200 and 1651 cm1, and has the 1 H NMR spectrum given below. What is the structure of H? 0 ppm 8 7654 3 3 H 2 H 1 H 2 H 1 H 1 H 2 1

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