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

1‐chloro‐4‐(chloromethyl)benzene

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):

1‐(4‐chlorophenyl)methanamine

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.

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  • $\begingroup$ Please add a complete reference to the book you are referring to, and Please do not add hyphens after colons. $\endgroup$
    – andselisk ♦
    Commented Sep 9, 2021 at 10:41
  • $\begingroup$ 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. $\endgroup$
    – user55119
    Commented Sep 9, 2021 at 14:04
  • $\begingroup$ @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. $\endgroup$
    – Parth
    Commented Sep 9, 2021 at 15:44

1 Answer 1

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I think your book is wrong (what book is it?)

This statement from the Wikipedia page on Azo coupling here seems definitive enough:

In alkaline media, diazonium salt can react with most primary and secondary amines that exist as a free base and produce triazene

It also includes a reaction scheme showing a secondary amine (pyrrolidine) coupling with a phenyl diazonium salt.

enter image description here

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