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Provided detailed curved arrow mechanisms for the following reactions: |
Answer» SOLUTION : Fragmentation of the tetrahedral INTERMEDIATE with an amide anion leaving group (in this case RNH) is the obvious RATE determining step, because an amide anion is a POOR leaving group (An amide anion is a poorer leaving group than a hydroxide ion.) One could combine this step with the nitrogen anion protonation to avoid having an amide anion leaving group. This is reasonable, as the solvent is WATER, and the amine will he hydrogen bonded before it departs. However, in this reaction, the amide anion leaving group problem cannot be solved by protenation with `H_(3) O` because `H_(3)O.` is simply not present. The reaction medium is strongly basic, so any strong acid such as hydronium ion will be immediately neutralized. |
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