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Organic - Decreasing order of basicity of these nitrogens?
here is the question...i have to arrange these nitrogens in decreasing basicity
https://postimg.org/image/6xatjxrb3/
and here is my answer
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pls help
hi...thanks for answering but isnt pyridine more basic than (1) and (2) because its lone pairs are available for donation as it is not involved in resonance
1 Answer
- DrBob1Lv 74 years ago
You're correct - the tertiary amine (5) is the strongest.
It is followed by the two aromatic amines; (2) is a secondary amine and is stronger than the primary amine (1).
The next in order is the heterocyclic aromatic amine, (4), whose unshared electrons are distributed around the ring by resonance.
The least basic nitrogen atom is found in the nitrile group, (3). Remember that the sp hydrogen in an alkyne is quite acidic. A nitrile nitrogen is an equally poor base.
