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What is the mechanism for the reaction between an aldehyde and a primary amine to form an imine product? Provide the balanced chemical equation and explain the steps involved in the mechanism.

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ago by (139k points)
The reaction between an aldehyde and a primary amine to form an imine product is called imine formation. The balanced chemical equation for this reaction is:RCHO + HNR'2  RCH=NR' + H2OWhere R and R' are alkyl or aryl groups.The mechanism for this reaction involves the following steps:1. Nucleophilic attack: The nitrogen atom of the primary amine  HNR'2  acts as a nucleophile and attacks the carbonyl carbon of the aldehyde  RCHO . This results in the formation of a tetrahedral intermediate and the breaking of the carbonyl double bond  C=O .2. Proton transfer: A proton  H+  is transferred from the nitrogen atom of the tetrahedral intermediate to one of the oxygen atoms, forming an alcohol group  -OH  and a positively charged nitrogen atom  NR'2H+ .3. Elimination of water: The alcohol group  -OH  acts as a leaving group and is eliminated as a water molecule  H2O . This results in the formation of a double bond between the carbon and nitrogen atoms  C=N , creating the imine product  RCH=NR' .In summary, the mechanism for the reaction between an aldehyde and a primary amine to form an imine product involves nucleophilic attack, proton transfer, and elimination of water.
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