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Tri-t-butyl amine is more basic than di-t-butyl amine in chlorobenzene but is less basic in aqua solution.explain.

Tri-t-butyl amine is more basic than di-t-butyl amine in chlorobenzene but is less basic in aqua solution.explain.

Grade:12th pass

3 Answers

Vikas TU
14149 Points
7 years ago
In qaqua. soln. amines reacts different than in air.
The basicity or stability of any amine compound is vice versa in air and aq. soln. 
The order of baascicity in aq. would be oppsoite that of in air.
This is the Reason Tri-t-butyl amine is more basic than di-t-butyl amine in chlorobenzene.
Surajit Das
20 Points
7 years ago
The basic strength of an amine in water is not only determined by the electron availability on the nitrogen atom but also by the extent to which the conjugate acid formed by the uptake of proton can undergo solution by hydrogen bonding and so become stabilised. With the increase of electron releasing methyl groups,the availability of unshared electron pair on nitrogen increases and the amine become progressively more stable. Again, as the numer of hydrogen attached to the conjugate acid decreases the extent of solution by water molecule decreases .As a consequence the stability of conjugate acid decreases and become prograessively less basic But in chlorobenzene solution no such solvation effect comes into play and the availability of unshared electron pair on N-atom is the dominating factor and hence in chlorobenzene solution tri-t-butyl amine is more basic than Di -t-butyl amine .
Surajit Das
20 Points
7 years ago
The basic strength of an amine in water is not only determined by the electron availability on the nitrogen atom but also by the extent to which the conjugate acid formed by the uptake of proton can undergo solution by hydrogen bonding and so become stabilised. With the increase of electron releasing methyl groups,the availability of unshared electron pair on nitrogen increases and the amine become progressively more stable. Again, as the numer of hydrogen attached to the conjugate acid decreases the extent of solution by water molecule decreases .As a consequence the stability of conjugate acid decreases and become prograessively less basic But in chlorobenzene solution no such solvation effect comes into play and the availability of unshared electron pair on N-atom is the dominating factor and hence in chlorobenzene solution tri-t-butyl amine is more basic than Di -t-butyl amine .

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