When certain aromatic compounds are treated with

Chapter 22, Problem 23.48

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When certain aromatic compounds are treated with formaldehyde, CH2O, and HCl, the CH2Cl group is introduced onto the ring. This reaction is known as chloromethylation. chloromethylation ? 1 CH2O 1 HCl Piperonal CH2Cl CHO O O O O O O (a) Propose a mechanism for this example of chloromethylation. (b) The product of this chloromethylation can be converted to piperonal, which is used in perfumery and in artifi cial cherry and vanilla fl avors. How might the CH2Cl group of the chloromethylation product be converted to a CHO group?

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