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hemistry A-Level: Mechanism Help Please x

Hi, please can somebody draw the mechanism for phenyl benzene carboxylate (C6H6COOC6H5) undergoing hydrolysis under acidic conditions? I would really appreciate that! xx + happy new year!
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Original post by timeisgoingfast
Hi, please can somebody draw the mechanism for phenyl benzene carboxylate (C6H6COOC6H5) undergoing hydrolysis under acidic conditions? I would really appreciate that! xx + happy new year!

What level are you working at? A level? Which exam board? I don't think any exam boards do the mechanism for hydrolysis of an ester (but am happy to check).
Original post by Pigster
What level are you working at? A level? Which exam board? I don't think any exam boards do the mechanism for hydrolysis of an ester (but am happy to check).

If it is an A level question, it would be assumed to be a nucleophilic addition-elimination reaction (which is required for AQA).

Whilst ester hydrolysis isn’t explicitly named as an example to learn (if I remember correctly), it’s perfectly possible that knowledge of it could be required for a “suggest a possible mechanism” type question.
Original post by Pigster
What level are you working at? A level? Which exam board? I don't think any exam boards do the mechanism for hydrolysis of an ester (but am happy to check).

Hi, I am so sorry for the late reply. This was the question from the AQA A-level exam board: Thank you so much for your help, much appreciated! xx
Sorry for getting back late! Yes, it was something like that.
Original post by timeisgoingfast
Hi, I am so sorry for the late reply. This was the question from the AQA A-level exam board: Thank you so much for your help, much appreciated! xx

You don’t need the mechanism when working that out. You need to recognise that when an ester hydrolyses, you form an alcohol and either a carboxylic acid (if hydrolysed in acidic conditions) or a carboxylate salt (if hydrolysed in basic conditions).

The name phenyl benzenecarboxylate suggests that the ester can be derived from phenol (C6H5OH, hence phenyl) and benzoic / benzenecarboxylic acid (C6H5COOH, hence benzenecarboxylate). The latter compound is one of your four options (D).

You don’t need to worry about mechanisms for ester hydrolysis - these are undergad level for a reason. If you are interested, though, I have included some extra info in a spoiler.


Extra info if you are interested

(edited 1 month ago)
Thank you very much, much appreciated! xx

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