Treatment of W with CH3Li, followed by CH3I, affords compound Y (C7H14O) as the major

Chapter 23, Problem 23.71

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Treatment of W with CH3Li, followed by CH3I, affords compound Y (C7H14O) as the major product. Y shows a strong absorption in its IR spectrum at 1713 cm1, and its 1 H NMR spectrum is given below. (a) Propose a structure for Y. (b) Draw a stepwise mechanism for the conversion of W to Y. W Y O O [1] CH3Li [2] CH3I 1 H ppm 1H NMR of Y 8 7654 3 210

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