Based on the information provided in the student question, we can deduce the structure of the unknown compound step-by-step:
1. The molecular formula C6H14O indicates that the compound contains 6 carbon atoms, 14 hydrogen atoms, and 1 oxygen atom.
2. Since the compound is a liquid at room temperature and slightly soluble in water, it suggests the presence of a polar functional group, such as an alcohol (OH) group.
3. The reaction with sodium metal and the evolution of gas indicates that the compound likely contains an acidic hydrogen atom, which further supports the presence of an alcohol group.
Now, considering the possible constitutional isomers for the given molecular formula:
- Hexanol isomers (1-hexanol, 2-hexanol, 3-hexanol, etc.): These would all show a similar H-NMR spectrum due to the similar structure, and would meet the requirements of a liquid at room temperature and reacting with sodium metal to release gas.
- Methylpentanol isomers (2-methyl-2-pentanol, 3-methyl-2-pentanol, etc.): These isomers would also show similar H-NMR spectra, but would differ slightly from the hexanol isomers.
To assign a specific structure to the unknown compound, we would need more information about the H-NMR spectrum, such as peak positions, splitting patterns, and integration values. This additional data would help to identify the exact positions of the alcohol group and any branching in the carbon chain, allowing us to distinguish between different constitutional isomers.