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Compound (A) forms only proprionaldehyde (B) upon ozonolysis and reduction with (CH3)2S. Treatment of (A) with...

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Chemistry

Compound (A) forms only proprionaldehyde (B) upon ozonolysis andreduction with (CH3)2S. Treatment of (A) with aqueous chlorineaffords (C) (C6H13ClO). Exposure of (C) to aqueous NaOH producesracemate (D) (C6H12O). (Think about intramolecular SN 2 reactionWilliamson ether synthesis). Compound (D) is also formed by thereaction of peracid with (A). What are the structures of (A), (B),(C) and (D)? Illustrate and explain. Show mechanism of aqueouschlorine reaction and indicate the arrows and lone pairs.

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