Problem

As we will learn in Chapter 20, reaction of (CH3)2CO with LiC≡≡ CH followed by H2O affords...

As we will learn in Chapter 20, reaction of (CH3)2CO with LiC≡≡ CH followed by H2O affords compound D, which has a molecular ion in its mass spectrum at 84 and prominent absorptions in its IR spectrum at 3600–3200, 3303, 2938, and 2120 cm−1. D shows the following 1H NMR spectral data: 1.53 (singlet, 6 H), 2.37 (singlet, 1 H), and 2.43 (singlet, 1 H) ppm. What is the structure of D?

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