An unknown aromatic compound A, has the molecular formula C13H16. Compound A rea

Question

An unknown aromatic compound A, has the molecular formula C13H16. Compound A reacts with Br2/CCl4 to give a tetrabrominated compound, C13H16Br4. When compound A is treated with hot, basic permanganate solutoim followed by acide, three different molecules, B, C, D are produced. Compound B is identical to the product obtained by the side-chain oxidation of meta-xylene. Compound C, C3H6O has only one single peak absorbance in its nmr spectrum. Compound D, C2H4O2, is water-soluable. Find the structures for compound A, B, C, and D.

Explanation / Answer

H3-CH2-CH2-NO2("A") + Fe/conc.HCl --------------> CH3-CH2-CH2-NH2("B")

CH3-CH2-CH2-NH2 + NaNO2/HCl ---------------> CH3-CH2-CH2-OH("C")

CH3-CH2-CH2-OH("C") + CrO3 -----------------> CH3-CH2-CHO

A = CH3-CH2-CH2-NO2 (Nitro propane)

B = CH3-CH2-CH2-NH2 ( Propyl amine)

C = CH3-CH2-CH2-OH ( Propanol)

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