{"id":148977,"date":"2024-02-27T19:10:44","date_gmt":"2024-02-27T13:40:44","guid":{"rendered":"https:\/\/www.mapsofindia.com\/my-india\/?p=148977"},"modified":"2024-02-27T19:10:44","modified_gmt":"2024-02-27T13:40:44","slug":"an-amide-a-with-molecular-formula-chon-undergoes-hoffmann","status":"publish","type":"post","link":"https:\/\/www.mapsofindia.com\/my-india\/quiz\/an-amide-a-with-molecular-formula-chon-undergoes-hoffmann","title":{"rendered":"An amide \u2018A\u2019 with molecular formula C,H,ON undergoes Hoffmann…"},"content":{"rendered":"

An amide \u2018A\u2019 with molecular formula C,H,ON undergoes Hoffmann Bromamide degradation reaction to give amine \u2018B\u2019. B\u2019 on treatment with nitrous acid at 273-278 K form \u2018C\u2019 and on treatment with chloroform and ethanolic potassium hydroxide forms D\u2019. \u2018C\u201d on treatment, with ethanol gives \u2018E\u2019. Identify \u2018A\u2019, \u2018B\u2019, \u2018C\u2019 D\u2019 and \u2018E.\u2019 and write the sequence of chemical equations.<\/h3>\n

Ans.<\/h3>\n

To solve this problem, let’s analyze each step of the reactions involved:<\/h3>\n
    \n
  1. \n

    Hofmann Bromamide Degradation:<\/strong><\/h3>\n
      \n
    • \n

      Hoffmann Bromamide degradation is a reaction where an amide is treated with bromine and a strong base like sodium or potassium hydroxide to produce an amine.<\/h3>\n<\/li>\n
    • \n

      The amide ‘A’ reacts to form amine ‘B’.<\/h3>\n<\/li>\n
    • \n

      In this case, the amide ‘A’ with the molecular formula C\u2083H\u2087ON reacts.<\/h3>\n<\/li>\n<\/ul>\n<\/li>\n
    • \n

      Treatment with Nitrous Acid:<\/strong><\/h3>\n
        \n
      • \n

        Amine ‘B’ reacts with nitrous acid (HNO\u2082) to form a diazonium salt ‘C’ at a low temperature (273-278 K).<\/h3>\n<\/li>\n<\/ul>\n<\/li>\n
      • \n

        Treatment with Chloroform and Ethanolic Potassium Hydroxide:<\/strong><\/h3>\n
          \n
        • \n

          Diazonium salt ‘C’ reacts with chloroform (CHCl\u2083) and ethanolic potassium hydroxide (KOH in ethanol) to form an isocyanide ‘D’.<\/h3>\n<\/li>\n<\/ul>\n<\/li>\n
        • \n

          Treatment with Ethanol:<\/strong><\/h3>\n
            \n
          • \n

            Isocyanide ‘D’ reacts with ethanol to form an amine ‘E’.<\/h3>\n<\/li>\n<\/ul>\n<\/li>\n<\/ol>\n

            Based on the reactions described, the identities are as follows:<\/h3>\n
              \n
            • \n

              ‘A’: The amide with the molecular formula C\u2083H\u2087ON.<\/h3>\n<\/li>\n
            • \n

              ‘B’: The amine formed after Hofmann Bromamide degradation of ‘A’.<\/h3>\n<\/li>\n
            • \n

              ‘C’: The diazonium salt formed after treatment of ‘B’ with nitrous acid.<\/h3>\n<\/li>\n
            • \n

              ‘D’: The isocyanide formed after treatment of ‘C’ with chloroform and ethanolic potassium hydroxide.<\/h3>\n<\/li>\n
            • \n

              ‘E’: The amine formed after treatment of ‘D’ with ethanol.<\/h3>\n<\/li>\n<\/ul>\n

              The sequence of chemical equations is as follows:<\/h3>\n
                \n
              1. \n

                Hofmann Bromamide degradation: \ufffd\u2192Hofmann\u00a0Bromamide\ufffd<\/span>A<\/span>Hofmann\u00a0Bromamide<\/span><\/span><\/span><\/span>\u200b<\/span><\/span><\/span><\/span><\/span>B<\/span><\/span><\/span><\/span><\/span><\/h3>\n<\/li>\n
              2. \n

                Treatment with nitrous acid: \ufffd+HNO2(273-278\u00a0K)\u2192\ufffd<\/span>B<\/span>+<\/span><\/span>HNO<\/span>2<\/span><\/span><\/span>\u200b<\/span><\/span><\/span><\/span><\/span>(<\/span>273-278\u00a0K<\/span><\/span>)<\/span>\u2192<\/span><\/span>C<\/span><\/span><\/span><\/span><\/span><\/h3>\n<\/li>\n
              3. \n

                Treatment with chloroform and ethanolic potassium hydroxide: \ufffd+CHCl3+KOH\u00a0(in\u00a0ethanol)\u2192\ufffd<\/span>C<\/span>+<\/span><\/span>CHCl<\/span>3<\/span><\/span><\/span>\u200b<\/span><\/span><\/span><\/span><\/span>+<\/span><\/span>KOH\u00a0(in\u00a0ethanol)<\/span><\/span>\u2192<\/span><\/span>D<\/span><\/span><\/span><\/span><\/span><\/h3>\n<\/li>\n
              4. \n

                Treatment with ethanol: \ufffd+Ethanol\u2192\ufffd<\/span>D<\/span>+<\/span><\/span>Ethanol<\/span><\/span>\u2192<\/span><\/span>E<\/span><\/span><\/span><\/span><\/span><\/h3>\n<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"

                An amide \u2018A\u2019 with molecular formula C,H,ON undergoes Hoffmann Bromamide degradation reaction to give amine \u2018B\u2019. B\u2019 on treatment with nitrous acid at 273-278 K form \u2018C\u2019 and on treatment with chloroform and ethanolic potassium hydroxide forms D\u2019. \u2018C\u201d on treatment, with ethanol gives \u2018E\u2019. Identify \u2018A\u2019, \u2018B\u2019, \u2018C\u2019 D\u2019 and \u2018E.\u2019 and write the […]<\/p>\n","protected":false},"author":21830,"featured_media":114041,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[12119],"tags":[],"class_list":{"0":"post-148977","1":"post","2":"type-post","3":"status-publish","4":"format-standard","5":"has-post-thumbnail","7":"category-quiz"},"aioseo_notices":[],"_links":{"self":[{"href":"https:\/\/www.mapsofindia.com\/my-india\/wp-json\/wp\/v2\/posts\/148977","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.mapsofindia.com\/my-india\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.mapsofindia.com\/my-india\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.mapsofindia.com\/my-india\/wp-json\/wp\/v2\/users\/21830"}],"replies":[{"embeddable":true,"href":"https:\/\/www.mapsofindia.com\/my-india\/wp-json\/wp\/v2\/comments?post=148977"}],"version-history":[{"count":1,"href":"https:\/\/www.mapsofindia.com\/my-india\/wp-json\/wp\/v2\/posts\/148977\/revisions"}],"predecessor-version":[{"id":148978,"href":"https:\/\/www.mapsofindia.com\/my-india\/wp-json\/wp\/v2\/posts\/148977\/revisions\/148978"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.mapsofindia.com\/my-india\/wp-json\/wp\/v2\/media\/114041"}],"wp:attachment":[{"href":"https:\/\/www.mapsofindia.com\/my-india\/wp-json\/wp\/v2\/media?parent=148977"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.mapsofindia.com\/my-india\/wp-json\/wp\/v2\/categories?post=148977"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.mapsofindia.com\/my-india\/wp-json\/wp\/v2\/tags?post=148977"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}