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Which one is the correct order of acidity?

1. CH≡CH > CH2=CH2 > C≡CH > CH2=CH−CH3
2. CH≡CH > CH2=CH−CH3 > CH2=CH2 > C≡CH
3. CH3−CH3 > CH2=CH2 > CH2=CH−CH3 > C≡CH
4. CH≡CH > CH2=CH2 > CH2=CH−CH3 > CH≡CH

Correct answer: CH≡CH > CH2=CH−CH3 > CH2=CH2 > C≡CH

Solution

The correct order of acidity is determined by the hybridization of the carbon atom bonded to the acidic hydrogen. sp-hybridized carbons (as in CH≡CH) are more acidic than sp2 (as in CH2=CH2) and sp3 (as in CH3−CH3). Thus, CH≡CH > CH2=CH−CH3 > CH2=CH2 > C≡CH is correct.

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