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












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.
Check out our Code of Conduct.







$endgroup$

















    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









    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.







    $endgroup$















      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.
      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






      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 1 hour ago









      orthocresol

      38.7k7113235




      38.7k7113235






      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.









      asked 1 hour ago









      Jhagrut LalwaniJhagrut Lalwani

      161




      161




      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.





      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.






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






















          1 Answer
          1






          active

          oldest

          votes


















          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











          Your Answer





          StackExchange.ifUsing("editor", function () {
          return StackExchange.using("mathjaxEditing", function () {
          StackExchange.MarkdownEditor.creationCallbacks.add(function (editor, postfix) {
          StackExchange.mathjaxEditing.prepareWmdForMathJax(editor, postfix, [["$", "$"], ["\\(","\\)"]]);
          });
          });
          }, "mathjax-editing");

          StackExchange.ready(function() {
          var channelOptions = {
          tags: "".split(" "),
          id: "431"
          };
          initTagRenderer("".split(" "), "".split(" "), channelOptions);

          StackExchange.using("externalEditor", function() {
          // Have to fire editor after snippets, if snippets enabled
          if (StackExchange.settings.snippets.snippetsEnabled) {
          StackExchange.using("snippets", function() {
          createEditor();
          });
          }
          else {
          createEditor();
          }
          });

          function createEditor() {
          StackExchange.prepareEditor({
          heartbeatType: 'answer',
          autoActivateHeartbeat: false,
          convertImagesToLinks: false,
          noModals: true,
          showLowRepImageUploadWarning: true,
          reputationToPostImages: null,
          bindNavPrevention: true,
          postfix: "",
          imageUploader: {
          brandingHtml: "Powered by u003ca class="icon-imgur-white" href="https://imgur.com/"u003eu003c/au003e",
          contentPolicyHtml: "User contributions licensed under u003ca href="https://creativecommons.org/licenses/by-sa/3.0/"u003ecc by-sa 3.0 with attribution requiredu003c/au003e u003ca href="https://stackoverflow.com/legal/content-policy"u003e(content policy)u003c/au003e",
          allowUrls: true
          },
          onDemand: true,
          discardSelector: ".discard-answer"
          ,immediatelyShowMarkdownHelp:true
          });


          }
          });






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










          draft saved

          draft discarded


















          StackExchange.ready(
          function () {
          StackExchange.openid.initPostLogin('.new-post-login', 'https%3a%2f%2fchemistry.stackexchange.com%2fquestions%2f108163%2fwhat-is-the-role-of-ammonium-chloride-in-the-workup-of-a-grignard-reaction%23new-answer', 'question_page');
          }
          );

          Post as a guest















          Required, but never shown

























          1 Answer
          1






          active

          oldest

          votes








          1 Answer
          1






          active

          oldest

          votes









          active

          oldest

          votes






          active

          oldest

          votes









          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












          $begingroup$

          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.










          draft saved

          draft discarded


















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













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












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
















          Thanks for contributing an answer to Chemistry Stack Exchange!


          • Please be sure to answer the question. Provide details and share your research!

          But avoid



          • Asking for help, clarification, or responding to other answers.

          • Making statements based on opinion; back them up with references or personal experience.


          Use MathJax to format equations. MathJax reference.


          To learn more, see our tips on writing great answers.




          draft saved


          draft discarded














          StackExchange.ready(
          function () {
          StackExchange.openid.initPostLogin('.new-post-login', 'https%3a%2f%2fchemistry.stackexchange.com%2fquestions%2f108163%2fwhat-is-the-role-of-ammonium-chloride-in-the-workup-of-a-grignard-reaction%23new-answer', 'question_page');
          }
          );

          Post as a guest















          Required, but never shown





















































          Required, but never shown














          Required, but never shown












          Required, but never shown







          Required, but never shown

































          Required, but never shown














          Required, but never shown












          Required, but never shown







          Required, but never shown







          Popular posts from this blog

          Polycentropodidae

          Magento 2 Error message: Invalid state change requested

          Paulmy