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I got that following my solution i get the product is 3HCO2H but the given answer is 3HCHO

  • $\begingroup$ Each carbon has two bonds to oxygen and two bonds to hydrogen, there is no oxidant present. How do you get HCOOH as product? $\endgroup$
    – Waylander
    Jan 6 '19 at 12:12

This compound is a special type of ether called an acetal. An acetal is a functional group with two alkoxy groups attached to the same carbon atom. They hydrolyze in aqueous acid to form aldehydes and ketones. The pair of carbon-oxygen single bonds is replaced by a carbon-oxygen double bond. The mechanism can be similar enough to what you drew, though an SN1-like mechanism is also reasonable.

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The carboxylic acid cannot form. There are two hydrogen atoms attached at that carbon atom, and they need to remain in the structure of the product. In order for the carboxylic acid to form, you would need to displace a hydrogen atom with a hydroxy group, not a likely step in a mechanism. When in doubt draw in the implicit hydrogen atoms.

  • $\begingroup$ For my interested what software did you use to draw the mechanism for this or was it an image you found? $\endgroup$
    – H.Linkhorn
    Jan 7 '19 at 18:37
  • $\begingroup$ I used ChemDoodle by iChemLabs: chemdoodle.com. It's not free, but it is inexpensive compared to ChemDraw, and there is a student discount. $\endgroup$
    – Ben Norris
    Jan 7 '19 at 21:44

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