How do you form imines?

1 Answer
anor277
Aug 1, 2016

By a condensation reaction:

#"Ketone + amine "rarr " Imine + water"#

Explanation:

Typically, the amine and the ketone are heated at reflux in toluene or benzene in a Dean Stark trap. The distillate, which contains the solvent, and water as an azeotrope, collects in the trap, where the water content may be measured, and extent of reaction determined.

#R_2C(=O) + H_2NR''# #rarr# #R_2C=NR'' + H_2O#.

There are many variations on this theme. Sometimes, a reagent (such as #TiCl_4#) is added to react with the water produced. The reaction between amine and ketone is slow; the reaction between amine and aldehyde is rapid. Why should this be?

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