Treatment of 2-butanone (CH3COCH2CH3) with strong base followed by CH3I forms a compound

Chapter 14, Problem 14.66

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Treatment of 2-butanone (CH3COCH2CH3) with strong base followed by CH3I forms a compound Q, which gives a molecular ion in its mass spectrum at 86. The IR (> 1500 cm1 only) and 1 H NMR spectrum of Q are given below. What is the structure of Q? 8 1H NMR of Q 7654 3 H 1 H 6 H 3210 ppm % Transmittance 100 50 0 4000 2000 3500 1500 3000 2500 Wavenumber (cm1)

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