The alkane formed by hydrogenation of (S)-4-methyl-1-hexyne is optically active, but the

Chapter 9, Problem 9.28

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The alkane formed by hydrogenation of (S)-4-methyl-1-hexyne is optically active, but the one formed by hydrogenation of (S)-3-methyl-1-pentyne is not. Explain. Would you expect the products of hydrogenation of these two compounds in the presence of Lindlar palladium to be optically active?

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