Which of the following compounds exhibits the greatest acidic character and reacts readily with sodium amide () to release ammonia gas?
Answer and explanation
Correct answer: C. Propyne
- Step 1: Acidity of hydrocarbons correlates with the -character of the hybrid orbital holding the conjugate base's negative charge.
- Step 2: The terminal hydrogen of an alkyne is bonded to an -hybridized carbon with -character, making it highly electronegative and stabilizing the carbanion.
- Step 3: Propyne () is acidic enough to be deprotonated by strong bases such as (conjugate acid has ): .
Answer
Propyne ().
Why not the others: Ethene has carbons ( -character, ) and does not react with ; Ethane has carbons ( -character, ); Benzene has carbons ().
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