Basicity Comparison:
Lithium benzoate: This is a salt formed from the reaction of benzoic acid and lithium hydroxide. Benzoic acid is a weak acid, meaning its conjugate base, the benzoate ion, is a weak base. Therefore, lithium benzoate is a weak base.
4-Lithium nitrobenzoate: The nitro group (-NO2) is an electron-withdrawing group, meaning it pulls electron density away from the carboxylate group. This makes the conjugate base (4-nitrobenzoate) less stable and decreases its basicity. Hence, 4-Lithium nitrobenzoate is a weaker base than lithium benzoate.
Phenylacetylene: This compound is an alkyne with a phenyl group. While the triple bond can theoretically be protonated, it's not a strong base. The phenyl ring is weakly electron-donating, but this effect is not enough to make phenylacetylene a significant base.
Overall:
Lithium benzoate > 4-Lithium nitrobenzoate > Phenylacetylene