Product of cyclohexanone/benzaldehyde with a substituted amine?

1 Answer
May 14, 2016

You should get an imine: R-C=NR'_2

Explanation:

A primary amine, RNH_2 should react with an aldehyde, R'C(=O)H according to the following equation:

RNH_2 + H(O=)CR' rarr RN=C(H)R' + H_2O (i)

And with a ketone:

RNH_2 + (O=)CR'R rarr RN=C(H)R'R + H_2O (ii)

Reaction (i) is usually very facile; sometimes you do not even need to use solvent, and you just add amine to aldehyde and remove the water. Formation of an imine from a ketone to give a ketimine is a little bit harder; you may have heat under reflux and remove the water produced; the carbonyl on the ketone is much more sterically hindered than the aldehyde. Both unsaturated nitrogen compounds tend to be a little bit unstable, so they are usually used directly.