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Compound X, a Geminal Dihalide, Is Exposed to Excess Strong

question 75

Essay

Compound X, a geminal dihalide, is exposed to excess strong base (excess NaNH2 then H2O) to produce an alkyne (compound Y). Alkyne Y is a terminal alkyne, has a molecular formula of C5H8, and has exactly 4 distinct resonances in the (proton-decoupled) 13C NMR spectrum. What are the two possible structures for compound X?


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