When 3,3-dichloropentane is treated with excess sodium a
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When 3,3-dichloropentane is treated with excess sodium amide in liquid ammonia, the initial product is 2-pentyne: Howeve
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When 3,3-dichloropentane is treated with excess sodium amide in liquid ammonia, the initial product is 2-pentyne: However, under these conditions, this internal alkyne quickly isomerizes to form a terminal alkyne that is subsequently deprotonated to form an alkynide ion: The isomerization process is believed to occur via a mechanism with the following four steps: (1) deprotonate, (2) protonate, (3) deprotonate, and (4) protonate. Using these four steps as a guide, try to draw the mechanism for isomerization using resonance structures whenever possible. Explain why the equilibrium favors formation of the terminal alkyne.
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