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On our exam in organic chemistry, there was a question that I failed to answer correctly. The question is about the Baeyer-Villiger esterification of propiophenone or ethyl phenyl ketone:

1‐phenylpropan‐1‐one

On the exam, I answered with this structure:

ethyl benzoate

But when the exam paper came back, I learned that the answer was where the oxygen is inserted adjacent to the aromatic ring:

phenyl propanoate

How can I resolve this dilemma of mine so I can prevent this mistake from happening?

andselisk
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Kent de los Reyes
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    Google for "migratory aptitude Baeyer-Villiger", there will surely be one site (maybe even on Stack Exchange) explaining it. There's no point memorising the list without first understanding the reaction mechanism, so make sure you know that first (your question doesn't give any indication of what you know about the reaction, beyond that it inserts oxygen atoms next to carbonyl groups). – orthocresol Aug 31 '19 at 17:16
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    @Kent de los Reyes: In addion to the Baeyer-Villiger reaction, there a few rearrangement reactions taught at about the same level of organic chemistry 101 with residues moving with different ease. Have a look for example on pinacolon rearrangement of diols, or Beckmann rearrangement of oximes (e.g., to access precursors of nylon). – Buttonwood Sep 01 '19 at 21:41

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