NCERT Class XI Chemistry Hydrocarbons Solutions

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Question : 18
Total: 25
Arrange benzene, n-hexane and ethyne in decreasing order of acidic behaviour. Also give reason for this behaviour.
Solution:  
The decreasing order of acidity is:

Acidic strength of any compound is defined as its ability to release H atom as H+ . This atom to which H is attached is highly electronegative. Such atoms tend to pull the bond pair of electrons towards themselves thereby polarising the bond and creating δ+ charge on H.
In the compounds in question, the H is attached to carbon atom which does not have a very high electronegativity value. Moreover, the electronegativity of carbon is somewhat increased if the s-character of its hybridised orbitals is high. Greater is the s-character of carbon, greater is its electronegativity as a result of which, the bond pair of electrons of the C – H bond moves towards carbon atom, creating a partial positive charge on H and facilitating its release as H+.
Based on this the order of acidic strength may be predicted as

Hybridization of Cspsp2 sp3
% s - character 50 % 33 % 25 %

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