The reaction of an aldehyde or ketone with a primary amine or ammonia ( or ammonia derivative, hydroxylamine, hydrazine, etc.) leads to formation of an imine (double bond between nitrogen and carbon). This form is also called a Schiff's base. As with secondary amines, the reaction begins with the formation of a tetrahedral carbinolamine through nucleophilic addition of the amine to the carbonyl group of the aldehyde or ketone. The carbinolamine is not stable because of the unequal tug of war across the central carbon between the two electronegative elements oxygen and nitrogen. The central carbon is like an electron deficient rope in a tug of war between two electron greedy elements, oxygen and nitrogen. If the nucleophile was a primary amine, the nitrogen loses a hydrogen ion so that the bonding electrons can shift to the central carbon (to satisfy the pull of oxygen). Oxygen can then depart, joining with a proton to become water. The resulting form with a double bond between nitrogen and carbon is an imine, or Schiff's base.












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