Predict the structures of compounds A, B, and C: A is an unbranched C6 alkyne that is

Chapter 7, Problem 7.54

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Predict the structures of compounds A, B, and C: A is an unbranched C6 alkyne that is also a primary alcohol. B is obtained from A by use of hydrogen and nickel boride catalyst or dissolving metal reduction. C is formed from B on treatment with aqueous acid at room temperature. Compound C has no infrared absorption in either the 16201680-cm-1 or the 35903650-cm-1 region. It has an index of hydrogen deficiency of 1 and has one chirality center but forms as the racemate

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