Question

What reaction could occur with an imine if it sits out on the benchtop that would cause it to revert back to para-toluidine and ortho-vanilin (the starting materials)? If sodium borohydride is added to these starting materials, which one would react to give a new product after neutralizing workup? what is the structure of this product?

Answer 1

Answer:

If an imine sits out on the benchtop and the atmosphere is sufficiently humid that would definitely cause the hydrolysis of imine which would revert to its starting materials such as an aldehyde(or ketone) and an amine.

In this case, it is given that the starting materials are para-toluidine and ortho-vanilin for the said imine. Between para-toluidine and ortho-vanilin, the para-toludine is having the reducible aldehyde group. Hence, this one will react with NaBH4 to give the respective primary alcohol functional in place of the aldehyde group. The structure of the product can be seen in the attached image.