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












9












$begingroup$


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






organic-chemistry experimental-chemistry grignard-reagent







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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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$endgroup$

















    9












    $begingroup$


    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






    organic-chemistry experimental-chemistry grignard-reagent







    share|improve this question









    New contributor




    Jhagrut Lalwani is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
    Check out our Code of Conduct.







    $endgroup$















      9












      9








      9


      2



      $begingroup$


      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






      organic-chemistry experimental-chemistry grignard-reagent







      share|improve this question









      New contributor




      Jhagrut Lalwani is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
      Check out our Code of Conduct.







      $endgroup$




      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




      organic-chemistry experimental-chemistry grignard-reagent






      share|improve this question









      New contributor




      Jhagrut Lalwani is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
      Check out our Code of Conduct.











      share|improve this question









      New contributor




      Jhagrut Lalwani is a new contributor to this site. Take care in asking for clarification, commenting, and answering.
      Check out our Code of Conduct.









      share|improve this question




      share|improve this question








      edited 12 hours ago









      orthocresol♦

      38.7k7113235




      38.7k7113235






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      asked 13 hours ago









      Jhagrut LalwaniJhagrut Lalwani

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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











          $endgroup$









          • 2




            $begingroup$
            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
            11 hours ago






          • 2




            $begingroup$
            Yes, coud use that or something like sodium dihydrogen phosphate.
            $endgroup$
            – Waylander
            11 hours ago











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          1 Answer
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          13












          $begingroup$

          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











          $endgroup$









          • 2




            $begingroup$
            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
            11 hours ago






          • 2




            $begingroup$
            Yes, coud use that or something like sodium dihydrogen phosphate.
            $endgroup$
            – Waylander
            11 hours ago
















          13












          $begingroup$

          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











          $endgroup$









          • 2




            $begingroup$
            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
            11 hours ago






          • 2




            $begingroup$
            Yes, coud use that or something like sodium dihydrogen phosphate.
            $endgroup$
            – Waylander
            11 hours ago














          13












          13








          13





          $begingroup$

          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 12 hours ago









          orthocresol♦

          38.7k7113235




          38.7k7113235










          answered 12 hours ago









          WaylanderWaylander

          6,15211123




          6,15211123








          • 2




            $begingroup$
            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
            11 hours ago






          • 2




            $begingroup$
            Yes, coud use that or something like sodium dihydrogen phosphate.
            $endgroup$
            – Waylander
            11 hours ago














          • 2




            $begingroup$
            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
            11 hours ago






          • 2




            $begingroup$
            Yes, coud use that or something like sodium dihydrogen phosphate.
            $endgroup$
            – Waylander
            11 hours ago








          2




          2




          $begingroup$
          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
          11 hours 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
          11 hours ago




          2




          2




          $begingroup$
          Yes, coud use that or something like sodium dihydrogen phosphate.
          $endgroup$
          – Waylander
          11 hours ago




          $begingroup$
          Yes, coud use that or something like sodium dihydrogen phosphate.
          $endgroup$
          – Waylander
          11 hours ago










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










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
















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