# Which amines show N−N coupling reaction?

We add 1 equivalent of $$\ce{KCN}$$ followed by catalytic reduction via Lindlar's reagent $$(\ce{H2}/\ce{Pt})$$ to 4-chlorobenzyl chloride (1).

Verify whether the product (P) obtained will undergo an N−N coupling reaction with a diazonium salt or not.

According to me, it should because I find no valid reason as to why it shouldn't. The product P that I obtained was 4-chlorobenzylamine (2):

But the book mentions that it won't. That made me wonder if there are some amines that don't participate in coupling reactions, or is it because of something else.

• Please add a complete reference to the book you are referring to, and Please do not add hyphens after colons. Sep 9 '21 at 10:41
• Shouldn't your first line read "We add 1 equivalent of KCN to 4-chlorobenzyl chloride (1) followed by catalytic reduction via Lindlar's reagent (H2/Pt)". If so, structure 2 is missing a methylene group. Sep 9 '21 at 14:04
• @user55119 Yes.I was trying to say that. I think after the “editing process” there might be some issues(with regards to question’s language) here and there. Sep 9 '21 at 15:44