Q. What is the name of this unknown compound? Additional info: Unknown compound

Question

Q. What is the name of this unknown compound?

Additional info: Unknown compound was insoluble in all solvents (water, ether, NaOH, NaHCO3, HCl and H2SO4). During the bromine/methyl chlodride test there was no decolorization indicating a negative test. The Baeyer test was negative and the aluminium chloride/chloroform test was positive. The refractive index was 1.4973 @ 20 degrees celsius. During distillation the boiling point of the first 10 drops was 68.4-84.1 degrees celsius, and the rest of the distillate was at a range of 85.3-137.2 degrees celsius

Explanation / Answer

It is Toulene, C6H5CH3.

Since it is non polar in nature hence won't soluble in the above mentioned solvents and negative Baeyers test but undergo positive Friedal - Craft's reaction with Alcl3 and CHCl3.

It has boiling point 110°C and refractive index 1.4973.

Peaks at 3015, 2921 are due to Aromatic =CH stretch and sp3 CH stretches. And peak at 1613 is due to c=c bond strech.

For monosubstitution, there are two peaks at 690&766.

Hence it is Aromatic hydrocarbon, toulene.

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