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Question
Arrange the following.
In decreasing order of basic strength in gas phase (C2H5)NH2, (C2H5)NH, (C2H5)3N and NH3.
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Solution
In the gas phase, solvent effects i.e., stabilization of the conjugate acids due to H-bonding, are absent. Therefore, in the gas phase, basic strength mainly depends upon the +I effect of the alkyl groups. Since the +I effect increases with the number of alkyl groups, therefore the basic strength of the amines decreases as the number of ethyl groups decreases from three in (C2H5)3N to two in (C2H5)2NH to one in C2H5NH2 and zero in NH3.
Basic strength in the gas phase decreases in the order is, (C2H5)3N > (C2H5)NH2 > (C2H5)NH > NH3.
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