Which of the following organic compounds exhibit sufficient acidic character to react completely wit — GOC and Organic Chemistry Basics Chemistry Question
Question
Which of the following organic compounds exhibit sufficient acidic character to react completely with sodium amide ($NaNH_2$), evolving ammonia gas ($NH_3$) as a byproduct?
Answer: A,B,C,D
💡 Solution & Explanation
Sodium amide ($NaNH_2$) contains the extremely strong base, the amide ion ($NH_2^-$). It can abstract protons from any compound more acidic than ammonia ($NH_3$, $pKa \approx 38$). This includes terminal alkynes ($pKa \approx 25$), alcohols ($pKa \approx 16$), phenols ($pKa \approx 10$), and carboxylic acids ($pKa \approx 5$). Thus, all the given compounds will react.
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