QuestionJuly 26, 2025

Which of the species below is less basic than acetylide? CH_(3)MgBr CH_(3)ONa CH_(3)Li both A and C all of the above

Which of the species below is less basic than acetylide? CH_(3)MgBr CH_(3)ONa CH_(3)Li both A and C all of the above
Which of the species below is less basic than acetylide?
CH_(3)MgBr
CH_(3)ONa
CH_(3)Li
both A and C
all of the above

Solution
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Answer

CH_{3}ONa Explanation 1. Identify the basicity of acetylide Acetylide ion (C \equiv C^-) is a strong base due to its negative charge and sp-hybridized carbon. 2. Compare with CH_{3}MgBr CH_{3}MgBr (Grignard reagent) acts as a strong base/nucleophile, similar in strength to acetylide. 3. Compare with CH_{3}ONa CH_{3}ONa (sodium methoxide) is a strong base but less basic than acetylide due to resonance stabilization in methoxide. 4. Compare with CH_{3}Li CH_{3}Li is a very strong base, comparable to acetylide, often stronger due to the carbanion character. 5. Determine which are less basic Only CH_{3}ONa is less basic than acetylide.

Explanation

1. Identify the basicity of acetylide<br /> Acetylide ion ($C \equiv C^-$) is a strong base due to its negative charge and sp-hybridized carbon.<br />2. Compare with $CH_{3}MgBr$<br /> $CH_{3}MgBr$ (Grignard reagent) acts as a strong base/nucleophile, similar in strength to acetylide.<br />3. Compare with $CH_{3}ONa$<br /> $CH_{3}ONa$ (sodium methoxide) is a strong base but less basic than acetylide due to resonance stabilization in methoxide.<br />4. Compare with $CH_{3}Li$<br /> $CH_{3}Li$ is a very strong base, comparable to acetylide, often stronger due to the carbanion character.<br />5. Determine which are less basic<br /> Only $CH_{3}ONa$ is less basic than acetylide.
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