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Which amongst the following is the strongest acid?

1. CHBr3
2. CHI3
3. CH(CN)3
4. CHCl3

Correct answer: CH(CN)3

Solution

In CH(CN)3 the three electron-withdrawing -CN groups delocalize/stabilize the negative charge of the conjugate carbanion most effectively (pKa ~ -5), making it by far the strongest acid among the four.

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