Questions: Which of the following is less basic than acetylide. A. BuLi B. NaNH2 C. NaOCH3 A and C B and C

Transcript text: Which of the following is less basic than acetylide. A. BuLi B. $\mathrm{NaNH}_{2}$ C. $\mathrm{NaOCH}_{3}$ $A$ and $C$ $B$ and $C$

Solution

Solution Steps

Step 1: Understand the Basicity of Acetylide

Acetylide ions ($\text{C}\equiv\text{C}^-$) are strong bases due to the high electron density on the carbon atom. They are typically formed by deprotonating terminal alkynes with strong bases.

Step 2: Compare Basicity of Given Compounds

BuLi (Butyllithium): This is a very strong base, often used to deprotonate compounds that are less acidic than terminal alkynes. It is more basic than acetylide.
$\mathrm{NaNH}_{2}$ (Sodium amide): This is also a strong base, commonly used to deprotonate terminal alkynes to form acetylide ions. It is comparable in basicity to acetylide.
$\mathrm{NaOCH}_{3}$ (Sodium methoxide): This is a weaker base compared to the other two. It is less basic than acetylide.

Step 3: Determine Which Compounds are Less Basic than Acetylide

From the comparison, $\mathrm{NaOCH}_{3}$ is less basic than acetylide, while $\mathrm{BuLi}$ and $\mathrm{NaNH}_{2}$ are not.