Question

Rank the following acids in order of decreasing acidity. H2O NH3 H2C=CH2 II CH3CH3 III HCECH IV I V O V > I > IV > II > III O

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Answer #1

Decreaing order of acidity is

I > IV > V > II > III

As H2O is most acidic as conjugate base has negative charge on oxygen which is more electronegative than N and C(sp, sp2, sp3). Then ethyne is second more acidic as sp hybridized carbon is more electronegative than N, so conjugate base of ethyne is more stable than conjugate base of NH3. Then NH3 is more acidic than ethene and ethene is more acidic than ethane as N is more electronegative than sp2 hybridized C and sp2 hybridized C is more electronegative than sp3 hybridized C.

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