research team synthesizes a novel organic compound 'X' with the molecular formula C5H8O2. When 'X' is treated with a deuterated acid (D2O), a single deuterium atom replaces a hydrogen atom, forming compound 'Y' (C5H7DO2). 'X' does not react with 2,4-Dinitrophenylhydrazine (2,4-DNP) but does react with both Tollens' reagent and

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter21: Benzene And The Concept Of Aromaticity
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Problem 21.63P
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"A research team synthesizes a novel organic compound 'X' with the molecular formula C5H8O2. When 'X' is treated with a deuterated acid (D2O), a single deuterium atom replaces a hydrogen atom, forming compound 'Y' (C5H7DO2). 'X' does not react with 2,4-Dinitrophenylhydrazine (2,4-DNP) but does react with both Tollens' reagent and Benedict's solution, forming a silver mirror and a red precipitate, respectively. Furthermore, 'X' undergoes catalytic hydrogenation over a palladium catalyst, consuming one mole of hydrogen to form a compound 'Z' (C5H10O2). Based on these observations, what is the most likely structure of compound 'X'?" A. Methyl vinyl ketone B. 3-Buten-2-one C. Acetoacetic ester D. 2-Hydroxypent-3-enal

 
 
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