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I came across some examples of organic compounds with acidic groups that didn't undergo the Clemmensen reduction. So, I was wondering which types of compounds the two reagents cannot reduce. Also, why?

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    $\begingroup$ Clemmensen relies on the carbonyl group protonating. If it is not the site of first protonation then it is not going to reduce. Similar for W-K; if the hydrazone cannot be deprotonated because another site is more acidic then the reaction will not proceed. $\endgroup$
    – Waylander
    Sep 28 at 14:24
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    $\begingroup$ related chemistry.stackexchange.com/questions/32174/… $\endgroup$
    – Mithoron
    Sep 28 at 14:32
  • $\begingroup$ @Waylander Okay, so if there was a carboxylic group, then the reduction wouldn't take place, right? $\endgroup$
    – CannedOrgi
    Sep 29 at 11:15
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    $\begingroup$ Pretty much. Once the carboxyl group is deprotonated you are trying to form a dianion for W-K. For Clemmensen the carboxyl group may well be site of first protonation but it may be easier for the carbonyl to be the site $\endgroup$
    – Waylander
    Sep 29 at 11:18

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