How do you distinguish between fluorene and acetanilide? Suggest methods other than melting point and chromatography.

IR; NMR; CHN analysis.

To distinguish between fluorene and acetanilide, you can employ additional methods other than relying solely on melting point determination and chromatography. Here are a few alternate techniques you can use:

1. Solubility Test: Dissolve both substances in different solvents and observe their solubility. Fluorene is highly soluble in non-polar solvents like hexane or ether, while acetanilide is more soluble in polar solvents like water or ethanol. By comparing their solubility behavior, you can differentiate between the two compounds.

2. Functional Group Tests: Conduct various chemical tests to identify the functional groups present in each compound. For example, the presence of an amide group in acetanilide can be confirmed by adding a few drops of concentrated sulfuric acid and observing the formation of a yellowish-brown solution. Fluorene, on the other hand, lacks the amide group and will not produce the same color change.

3. Spectroscopic Analysis: Perform infrared spectroscopy (IR) or nuclear magnetic resonance (NMR) on the substances. Each compound will have distinctive peaks or patterns in their spectral analysis due to the different functional groups present. By comparing their spectra, you can differentiate between fluorene and acetanilide.

4. Elemental Analysis: Perform a combustion or elemental analysis on each compound. This method determines the percent composition of carbon, hydrogen, and nitrogen in a substance. The results will differ between fluorene and acetanilide, allowing you to distinguish between them.

Remember, it is always important to use multiple methods in combination to ensure accurate distinction between two compounds.