In: Chemistry
Compound (A) forms only proprionaldehyde (B) upon ozonolysis and reduction with (CH3)2S. Treatment of (A) with aqueous chlorine affords (C) (C6H13ClO). Exposure of (C) to aqueous NaOH produces racemate (D) (C6H12O). (Think about intramolecular SN 2 reaction Williamson ether synthesis). Compound (D) is also formed by the reaction of peracid with (A). What are the structures of (A), (B), (C) and (D)? Illustrate and explain. Show mechanism of aqueous chlorine reaction and indicate the arrows and lone pairs.