What is the role of ammonium chloride in the workup of a Grignard reaction?












3












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In the following Grignard reaction, why is aqueous ammonium chloride used to get to the products?



Reaction of (3S)-3-methylcyclohexan-1-one with methylmagnesium bromide










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$endgroup$

















    3












    $begingroup$


    In the following Grignard reaction, why is aqueous ammonium chloride used to get to the products?



    Reaction of (3S)-3-methylcyclohexan-1-one with methylmagnesium bromide










    share|improve this question









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    Jhagrut Lalwani is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
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    $endgroup$















      3












      3








      3





      $begingroup$


      In the following Grignard reaction, why is aqueous ammonium chloride used to get to the products?



      Reaction of (3S)-3-methylcyclohexan-1-one with methylmagnesium bromide










      share|improve this question









      New contributor




      Jhagrut Lalwani is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
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      $endgroup$




      In the following Grignard reaction, why is aqueous ammonium chloride used to get to the products?



      Reaction of (3S)-3-methylcyclohexan-1-one with methylmagnesium bromide







      organic-chemistry experimental-chemistry grignard-reagent






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      share|improve this question








      edited 1 hour ago









      orthocresol

      38.7k7113235




      38.7k7113235






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      asked 1 hour ago









      Jhagrut LalwaniJhagrut Lalwani

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          $begingroup$

          Ammonium chloride ($ce{NH4Cl}$) is the work-up reagent that quenches the magnesium alkoxide product of the Grignard addition. It is the reagent of choice as it is a proton source without being acidic; acidic conditions could result in protonation of the tertiary alcohol product and elimination to the alkene. It also ensures that all inorganic salts of Mg will extract into the aqueous phase.






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          $endgroup$













          • $begingroup$
            Oh I actually never knew that! In that case, other weak acids can also be used right? For example, what about weak organic acids like ethanoic acid?
            $endgroup$
            – Tan Yong Boon
            14 mins ago











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          1 Answer
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          $begingroup$

          Ammonium chloride ($ce{NH4Cl}$) is the work-up reagent that quenches the magnesium alkoxide product of the Grignard addition. It is the reagent of choice as it is a proton source without being acidic; acidic conditions could result in protonation of the tertiary alcohol product and elimination to the alkene. It also ensures that all inorganic salts of Mg will extract into the aqueous phase.






          share|improve this answer











          $endgroup$













          • $begingroup$
            Oh I actually never knew that! In that case, other weak acids can also be used right? For example, what about weak organic acids like ethanoic acid?
            $endgroup$
            – Tan Yong Boon
            14 mins ago
















          4












          $begingroup$

          Ammonium chloride ($ce{NH4Cl}$) is the work-up reagent that quenches the magnesium alkoxide product of the Grignard addition. It is the reagent of choice as it is a proton source without being acidic; acidic conditions could result in protonation of the tertiary alcohol product and elimination to the alkene. It also ensures that all inorganic salts of Mg will extract into the aqueous phase.






          share|improve this answer











          $endgroup$













          • $begingroup$
            Oh I actually never knew that! In that case, other weak acids can also be used right? For example, what about weak organic acids like ethanoic acid?
            $endgroup$
            – Tan Yong Boon
            14 mins ago














          4












          4








          4





          $begingroup$

          Ammonium chloride ($ce{NH4Cl}$) is the work-up reagent that quenches the magnesium alkoxide product of the Grignard addition. It is the reagent of choice as it is a proton source without being acidic; acidic conditions could result in protonation of the tertiary alcohol product and elimination to the alkene. It also ensures that all inorganic salts of Mg will extract into the aqueous phase.






          share|improve this answer











          $endgroup$



          Ammonium chloride ($ce{NH4Cl}$) is the work-up reagent that quenches the magnesium alkoxide product of the Grignard addition. It is the reagent of choice as it is a proton source without being acidic; acidic conditions could result in protonation of the tertiary alcohol product and elimination to the alkene. It also ensures that all inorganic salts of Mg will extract into the aqueous phase.







          share|improve this answer














          share|improve this answer



          share|improve this answer








          edited 1 hour ago









          orthocresol

          38.7k7113235




          38.7k7113235










          answered 1 hour ago









          WaylanderWaylander

          6,06211122




          6,06211122












          • $begingroup$
            Oh I actually never knew that! In that case, other weak acids can also be used right? For example, what about weak organic acids like ethanoic acid?
            $endgroup$
            – Tan Yong Boon
            14 mins ago


















          • $begingroup$
            Oh I actually never knew that! In that case, other weak acids can also be used right? For example, what about weak organic acids like ethanoic acid?
            $endgroup$
            – Tan Yong Boon
            14 mins ago
















          $begingroup$
          Oh I actually never knew that! In that case, other weak acids can also be used right? For example, what about weak organic acids like ethanoic acid?
          $endgroup$
          – Tan Yong Boon
          14 mins ago




          $begingroup$
          Oh I actually never knew that! In that case, other weak acids can also be used right? For example, what about weak organic acids like ethanoic acid?
          $endgroup$
          – Tan Yong Boon
          14 mins ago










          Jhagrut Lalwani is a new contributor. Be nice, and check out our Code of Conduct.










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