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6
Q:

Order of basicity of amines in gaseous state?

A) 2'> 1'> 3' > NH3 B) 3' > 2' > 1'> NH3
C) 1' > 2' > 3'> NH3 D) 2'> 3'> 1' > NH3

Answer:   B) 3' > 2' > 1'> NH3



Explanation:

The order of basicity in ammonia is different in gaseous phases vs. aqueous phases due to hydrogen bonding.

 

So in gaseous phases it's the well known: 3' > 2' > 1'> NH3. Just so we're on the same page, this is due to the inductive effect of electron donating alkyl groups--they destabilize the lone pair on nitrogen atom, making nitrogen more basic.

 

But in aqueous phase, the order is slightly different: 2'> 1'> 3' > NH3.

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