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A nitroalkane is treated with HONO and forms a product that is insoluble in alkali but becomes blue when alkali is added. Which nitroalkane is it?

1. CH3CH2NO2
2. CH3-CH(CH3)-CH2NO2
3. (CH3)2CHNO2
4. (CH3)3CNO2

Correct answer: (CH3)2CHNO2

Solution

With HNO2, a secondary nitroalkane forms a pseudonitrole, R2C(NO)(NO2), which is blue and insoluble in alkali. Primary nitroalkanes give nitrolic acids (red in alkali) and tertiary give no reaction; hence the compound is (CH3)2CHNO2.

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